Booking Virgin America to Hawaii: the bad, the good, and one weird old trick

While Virgin America doesn't have very many flights from where I live, I was still intrigued by the new, as of January 9, 2017, ability to book Virgin America flights using Alaska Airlines Mileage Plan miles, since I still have a slew of them left over from the days of the Bank of America Alaska Airlines debit card and Alaska's generous status match.

I don't need any help getting around the continental United States, but Virgin America flies to Hawaii and Mexico, so I decided to see what their award availability looked like.

As regular readers might expect, I took a brute force approach: for every date between January 10 and February 10, and between November 7 and December 7, 2017, I checked to see if there was at least one first class seat available from San Francisco to Honolulu and from San Francisco to Maui. I didn't check return flights.

In other words, I'm not trying to plan a trip, but just trying to get a sense of what kind of award space might be available for future reference.

Searching Alaska is the worst

Since Virgin America Elevate redemptions are revenue-based, it's not possible to search Virgin America's website for low-level award availability — you have to use Alaska's website instead.

The problem with this is two-fold. First, Alaska's award calendar doesn't allow you to filter by the number of stops you're willing to make, so the award calendar will show you the lowest award rate available across every possible itinerary.

That wouldn't be so bad except, additionally, Alaska doesn't allow you to filter by the cabin of service available for the entire trip. That means most dates will have at least one seat's worth of "low-level" first class award availability, since a combination of a short first class hop and long main cabin flight will price as a "low-level" award and appear on the award calendar.

To illustrate this, here's the November, 2017, calendar for first class flights between San Francisco and Honolulu:

And here's the actual 40,000-mile first class itinerary that Alaska returns:

The results

With that out of the way, let's see the results.

Here are the results of my search for a single first class award seat on the non-stop Virgin America flight between San Francisco and Honolulu:

  • November 7-December 7, 2017: 1 date (December 7)
  • January 10-February 10, 2017: 15 dates

And here are the results of my search for a single first class award seat between San Francisco and Maui:

  • November 7-December 7, 2017: 1 date (December 7)
  • January 10-February 10, 2017: 16 dates

I don't know anything about the flow of tourists between the Bay Area and Hawaii, so maybe late November is the high season and late January is the low season. Alternatively, Virgin America might open up a lot of first class award seats within 30 days of departure, which would be good to know if you have a flexible travel schedule.

One weird old trick to book Virgin America first class award seats

You may have noticed above I indicated the specific date, December 7, on which I was able to find a first class award seat to Hawaii. That date is significant because it's outside the Alaska calendar booking window (as of this writing; when you read this December 8 will serve the same function):

Once you view flights available on December 6, however, the engine is suddenly able to show flights on the December 7 as well:

I found this interesting enough that I searched for a number of other international destinations from San Francisco, and was able to find a first class award seat on every route I searched.

My tentative hypothesis is that people watching for the booking calendar to open up in order to book awards may not realize this extra day is available.

My alternate hypothesis is that Thursday, December 7, is some kind of holy day on which residents of the Bay Area are forbidden to travel, thus opening up more award seats than are otherwise available.

Conclusion

So, what have we learned?

  • First class award availability on Virgin America between the West Coast and Hawaii is fairly easy to find either in late January, or within 30 days of departure.
  • First class award availability between the West Coast and Hawaii and Mexico is fairly easy to find either one day after the Alaska "search" calendar ends, or on Thursday, December 7, 2017.

The world is full of nice people trying to give you advice

I'm lucky enough to have the opportunity to periodically get together with travel hackers around the country, whether it's at organized DO's, subscribers-only meetups, or spontaneous get-togethers while I'm traveling.

Almost invariably, the subject of affiliate bloggers comes up and someone will turn to me and say, "it was funny what you wrote about View from the Frugal Points Time, but when you meet him in person he's actually really nice."

I've heard this enough times now that it might be worth clearing some things up.

I'm not very nice (and I don't give advice)

I have met some nice people in my life, and I am somewhat in awe of them. You probably know the kind of person I'm talking about: people who always think before speaking, who are unfailingly polite, who seem to move through life leaving as small a wake as possible.

I'm not like that. I make snap judgments, I don't give people the benefit of the doubt, I take Donald Trump both literally and seriously. When readers offer to buy me a beer it doesn't occur to me to reciprocate.

I'm a jerk!

I also don't give advice. I go out every day and try to find ways to make myself and my readers miles, points, and cash. But all I know about my readers is that I don't know them well enough to give them, or anyone else, advice. So I don't.

I work for you

I suppose it must come across as corny to some readers, but when I say I work for you I'm not trying to be cute, I'm just explaining how this site works. I don't have affiliate managers breathing down my neck to get my conversions up. I don't have compliance managers telling me what I can and can't write and what font the terms and conditions have to be in. I get paid when people like my site enough to visit and subscribe.

The world is full of nice people trying to give you advice

Your Merrill Lynch stockbroker is a nice guy. He takes you and his other high-net-worth clients out for dinner (two entrée choices) a couple times a year to talk about market dynamics and the risks he sees in the year ahead. Then he churns your account and generates another commission.

Your insurance agent is definitely a nice guy. He listens very carefully to all your concerns about your health, your children's education, and your concerns about downsizing to a smaller house. Then he sells you a variable indexed annuity.

So it doesn't surprise me in the least that your affiliate blogger is a nice guy. He carefully responds to your questions and comments. He shakes your hand and looks you in the eye at Frequent Traveler University. Then he sells you a Chase Sapphire Preferred.

Being nice isn't enough

It may sound like I'm calling "being nice" some kind of stratagem or ruse people working on commission use to gain the trust of their clients in order to take advantage of them. But while there's some of that in the world, I don't profess to have any insight into the deepest recesses of either your stockbroker's or your affiliate blogger's soul.

The fact is that in the best case scenario your affiliate blogger is a nice guy who just happens to be in a line of work that requires him to put his interests before yours. Likewise there are coal mining engineers who got into coal extraction because they like being outdoors, not because they have anything against the ice caps.

I don't need to know anything about someone's heart of hearts to assess the impact of their choices on the world around them. 

Disclosure isn't enough

Your stockbroker, your insurance agent, and your affiliate blogger are all required to disclose their conflicts of interest, and do so dutifully. The problem is that disclosure of conflicts of interest does not have any impact on the quality of the advice provided, and may perversely lead you to trust the conflicted party more, not less.

Let me be clear: the logical response to "I may be compensated based on your choice of mutual fund/insurance product/credit card" is not to discount the advice given by 10%, or 20%, or 50%.

The logical response is to discount the advice given by 100%.

If you are not the customer, you're the product

It's tempting to say that some bloggers are "ethical" while others are "unethical," but I personally find the question of ethics orthogonal to this discussion, since the requirements of ethics may be satisfied by "full disclosure" without improving the observed result of too many readers signing up for credit cards that benefit the affiliate blogger rather than the reader.

No, the problem of affiliate bloggers pounding the drumbeat of constant, mounting urgency each time a particular card or issuer offers them an increased payout can't be solved by resorting to ethical considerations. It can only be solved by judgment.

So I'm judgmental. Which, along with being rash, brash, and cheap, is yet one more reason why, unlike your favorite affiliate blogger, I'm not a very nice guy.

Thoughts and feelings about BankAmericard Travel Rewards

The best deal in travel

In my opinion the best deal in travel hacking is likely the BankAmericard Travel Rewards credit card with Bank of America Preferred Rewards Platinum Honors. That combination turns every dollar in unbonused spend into 2.625 cents towards future travel redemptions.

That's not to say there isn't competition for best deal:

  • A Chase Ink Plus and Sapphire Reserve combination allows you to earn 5 Ultimate Rewards points per dollar spent at office supply stores and redeem them for 1.5 cents each on paid travel.
  • Likewise an Ink Plus combined with the Southwest Companion Pass allows you to redeem those 5 Ultimate Rewards points for (very roughly) 3.2 cents each on Wanna Get Away fares with Southwest when flying with your designated companion, the equivalent of earning 16% on your office supply store spend.
  • An American Express Premier Rewards Gold card and Platinum Business card would let you earn 2 Membership Rewards points at supermarkets and redeem them for 2 cents each towards premium-cabin airfare, plus enjoy the flexibility of Membership Rewards points transfers.

That said, I don't personally have a Travel Rewards card, and suspect the vast majority of travel hackers either don't have or don't use one. Here's everything you need to know about the pros and cons of BankAmericard Travel Rewards and Preferred Rewards with Bank of America.

You need to have a lot of money (occasionally)

To qualify for Platinum Honors with Bank of America Preferred Rewards, you need to have $100,000 in combined balances with:

  • Bank of America;
  • Merrill Lynch, the bank's full-service brokerage business;
  • and Merrill Edge, the bank's self-directed brokerage service.

Sound simple? Hang on tight.

To initially enroll in the program, you need to have an average daily balance over the preceding 3-month period of $20,000 or more (the minimum to qualify for the Gold tier in Preferred Rewards). Each month after that Bank of America checks to see if you're eligible for a higher tier: if you enroll with a 3-month daily average balance of $20,000, you'll be upgraded to the Platinum tier when your 3-month daily average balance reaches $50,000 and to the Platinum Honors tier when your 3-month daily average balance reaches $100,000. That "check" only happens once per month.

After you've reached a tier in Preferred Rewards you keep that status for 15 months. Technically you earn the status for 12 months and then have a 3-month grace period to requalify before being moved to a lower tier or removed from the program. [Edit 1/7/16: Please see Robert's comment for clarification on how the enrollment period and grace period work in practice.]

Three-month average daily balances are a funny thing. You could meet the $100,000 requirement over 3 months in any number of ways, including:

  • Month 1: $100,000. Month 2: $100,000. Month 3: $100,000.
  • Month 1: $0. Month 2: $150,000. Month 3: $150,000.
  • Month 1: $0. Month 2: $0. Month 3: $300,000.

All three variants produce an average daily balance of $100,000 over a 3-month period, but you must have an account for 3 months to qualify. You can't just deposit $300,000 in a new account and enroll in the Platinum Honors tier the following month.

Most people don't have that kind of money in cash, but you might. If you just sold a house or inherited some money, for example, you might have $300,000, and if you aren't in a rush to spend it, parking it with Bank of America for a month would qualify you for the Platinum Honors tier for the next 15 months.

Investing with Merrill Edge

Obviously, most people don't meet the Platinum Honors tier requirements that way. Instead, they open up a Merrill Edge account and move $100,000 or more in cash or securities into their account, and leave them there.

Note: I'm a passive, indexed investor, so all of the following is going to be from the point of view of passive indexed investing.

In writing this post I scoured the ends of the internet to find as complete and accurate information as possible regarding how to transfer, buy and hold Vanguard mutual funds and ETFs with Merrill Edge. Here's what I found.

  • Merrill Edge accountholders can buy shares of Vanguard ETF's and "Investor" shares of most if not all Vanguard mutual funds.
  • As a Platinum Honors accountholder you receive 100 free stock and ETF trades per month, so there would be no cost to purchase Vanguard ETF's with cash. Purchasing new Investor shares of Vanguard mutual funds has a $19.95 fee.
  • This creates an obvious chicken/egg problem: to get free ETF trades, you have to be Platinum Honors, but to be Platinum Honors, you have to have funds in your account.
  • Unless you want to park $100,000 in cash in your account, the obvious solution is to transfer $100,000 (or more) in existing securities from their current custodian.
  • Merrill Edge allows some, but not all, "Admiral" shares to be transferred in-kind from Vanguard. That means you are able to hold in a Merrill Edge account shares that cannot be purchased in a Merrill Edge account.
  • Once you hold Admiral shares with Merrill Edge you can reinvest dividends and capital gains, but you still can't purchase new shares. Admiral shares have the advantage of being lower cost than Investor shares and, in some cases, ETF shares (VTIAX is cheaper than VXUS, for example). You can read way more about this issue here.
  • If your Admiral shares can't be held by Merrill Edge, or if you intend to use Merrill Edge for ongoing contributions and don't want to hold two different share classes in your account, you can convert Admiral shares in all but four Vanguard mutual funds into ETF shares. You can also convert Admiral shares into Investor shares, but since Investor shares have higher fees than ETF's that's unlikely to be your lowest-cost move.
  • ETF shares can be moved in-kind from Vanguard to Merrill Edge, although fractional shares will be sold, not transferred. This may produce a taxable capital gain if the transfer is between taxable accounts.
  • [Edit 1/6/16: See reader EightBall's comment below for more on this issue, and this Boglehead forum post.]If you elect to reinvest dividends from an ETF, Merrill Edge will charge a 10% "fractional share liquidation fee" on any partial shares. In other words, they buy the whole number of shares your dividends can afford, then charge you 10% of the remainder as a convenience fee before depositing the rest in cash. To avoid that fee, you can elect to receive dividends in cash and manually purchase whole ETF shares, which sounds hellishly annoying. This is one reason I personally prefer Admiral shares to ETF's.

This may seem like a lot of trivia. But I'm laying it all out here for two reasons. First, it took me a couple hours of searching and reading to find the answers to all these questions, so hopefully putting it in one place saves somebody else the same trouble. Second, I truly believe the best way to build wealth is the long-term, automated, low-cost purchase of mutual funds tracking broad market indices.

Merrill Edge, like all brokerages, would like you to do as much short-term, manual, high-cost buying and selling of speculative securities as possible.

Merrill Edge new account bonuses

So you're a mid-career upper-middle-class professional, or early-career FIRE enthusiast, and you've got $100,000 sitting in your Vanguard account. You're intrigued by what your humble blogger earlier called "the best deal in travel hacking." The next step is to open a Merrill Edge account and transfer $100,000 in securities in-kind, right?

Not so fast.

Like many online brokerages, Merrill Edge offers signup bonuses for new customers who open accounts with qualifying balances. The standard Merrill Edge bonus is $100-$600 depending on the amount you deposit within 45 days of opening your account.

But that offer periodically goes as high as $1,000 for deposits of $200,000 or more. There's even a landing page for the higher offer, although it includes an expiration date of December 31, 2016.

If you're eager to get the process started of earning Preferred Rewards status and triggering the highest payout on the Travel Rewards credit card, then go ahead and get started. But if you're not in any hurry, then it may be worth waiting for that higher signup bonus to come around again. Even if you just deposit $100,000, the higher bonus pays out $250 more than the standard one, which it would certainly be nice to have in your retirement accounts happily compounding away.

Conclusion

I'm a long way from having $100,000 in my retirement account, so I won't personally be taking advantage of this deal any time particularly soon. But in this era of cheap and plentiful, but unbonused, manufactured spend I do believe earning 2.625% in travel rewards on all purchases is one of the best opportunities widely available — to those who can afford it.

Booking Southwest flights with Flexpoints and Ultimate Rewards

I previously wrote up my experience booking a Hyatt all-inclusive resort in Jamaica. That left the question of how to get there. While I'm not ready to be seduced by Southwest, I waited to pull the trigger a bit too long and the price difference between the nonstop Southwest flight and one-stop options on real airlines shrank enough to convince me to give them a shot, despite my reservations.

Chase Ultimate Rewards points and US Bank Flexpoints can be used to book Southwest flights

Southwest famously doesn't participate in the public Global Distribution System that real airlines use, which is why their fares don't show up on ITA Matrix, Google Flights, and online travel agencies (Google Flights will show you Southwest routes, but not fares).

But the Chase Ultimate Rewards travel center and US Bank Flexperks Travel Rewards travel contractor can book Southwest fares over the phone.

Redeeming Chase Ultimate Rewards points for travel on Southwest

To make an Ultimate Rewards redemption on Southwest call 866-951-6592.

Like all Ultimate Rewards travel redemptions, points are worth 1.25 cents each for travel on Southwest, and you can use any number of Ultimate Rewards points against the purchase price and pay the remainder in cash. After transferring points to Hyatt to pay for our stay in Jamaica, I didn't have quite enough Ultimate Rewards points left to pay for my partner's ticket, so I redeemed my entire Ultimate Rewards balance and paid the remaining amount with my Chase Ink Plus card, which should earn 2 Ultimate Rewards points per dollar if the purchase codes correctly as a Travel Center reservation.

Theoretically I could have redeemed my Ultimate Rewards balance for a cheaper Southwest fare, then cancelled that flight and used the value towards the ticket I really wanted while paying the difference with the card of my choice. Since this was my partner's ticket and as far as I know she doesn't even have a Rapid Rewards account, I decided to keep it simple and just book the tickets I really wanted.

After feeding the Ultimate Rewards agent the dates and flights I wanted, she came back with a price about $90 cheaper than the fare available online. I had heard of this happening before, so told her to go ahead and make the reservation. After giving her all of my partner's information and my credit card information, and waiting on hold for a while, she came back and told me that flight was not available.

After going back and forth a few times, it turned out what she really meant was that that fare wasn't available, which didn't surprise me, and she was ultimately able to book the fare I had found online.

The call took a total of 45 minutes.

Redeeming US Bank Flexpoints for travel on Southwest

To redeem Flexpoints for travel on Southwest call 888-229-8864. The "Rewards Center" US Bank uses is not open 24 hours a day, but has pretty reasonable hours, something like 7 am to 11 pm, Monday through Saturday (I didn't catch their Sunday hours, but they were closed at 10:50 pm Eastern on Sunday).

After taking down my trip details, the agent explained that in order to book international travel on Southwest he had to call them, get a fare quote, put the reservation on hold, and then return to confirm the fare and itinerary with me. He asked me if there was a particular fare I was expecting, which seemed like a common sense precaution to make sure we were looking at the same flights and dates. It was unclear to me whether the same procedure is required for domestic travel on Southwest.

While the Southwest Anytime fare I booked for my partner was still available for about $900, a Business Select fare was also available for $950. Since I was redeeming Flexpoints, I knew that either itinerary would cost 50,000 Flexpoints and I told the agent to look for the Business Select fare. He was happy to do so and, after putting me on hold for 25 minutes or so, returned with the same fare I had found online.

Since Southwest flights can't be booked online, he also waived the $25 phone booking fee.

The call took a total of 44 minutes. If it seems strange that the call took almost as long as my call with Chase did even though the agent was able to accurately find the correct fare on his first try, the reason is the two lengthy holds he placed me on while calling Southwest.

Adding your Rapid Rewards number

Neither agent asked for a Rapid Rewards number to add to the reservations, and I didn't ask since I was getting pretty bored of waiting on the phone. However, both agents provided the Southwest confirmation number, which made it easy to pull up the reservations on Southwest.com. The Flexperks Rewards Center also provided an "agency" confirmation number they use internally — be sure you get the Southwest confirmation number as well.

Strangely, I was unable to add my Rapid Rewards number to my reservation while logged into Southwest.com. After logging out, however, I was able to pull up my reservation and manually add my Rapid Rewards number, and the reservation immediately appeared in my account.

Fuel surcharges on Korean's SkyTeam partners

Last week I saw a flood of posts about Korean Air adding the ability to search and book SkyTeam partner awards online (for example). Since Korean Air SKYPASS is an Ultimate Rewards transfer partner, it's worth checking to see if there are any good values on their SkyTeam partners now that it can be done easily online.

The three most important things people know about Korean Air SKYPASS are:

  1. You can only book awards for yourself and a very tightly defined group of family members;
  2. SKYPASS awards pass along fuel surcharges;
  3. Korean Air's award "zone" definitions are unusually generous, with Hawaii located in North America and South America being treated as a single zone.

Being a literal-minded sort of person, I decided to see how bad those fuel surcharges are on all of the SkyTeam carriers departing from the United States.

Here's what I found.

Not bookable online

While I was able to find award space on these SkyTeam airlines using Delta's search engine, I couldn't pull up the same flights using SKYPASS:

  • Aeromexico to Latin America;
  • Alitalia to Italy;
  • Aerolineas Argentinas to Argentina.

The functionality may be added in the future, but for now I don't believe SkyTeam awards are bookable online using SKYPASS on those carriers.

Low fuel surcharges

Carriers that charge low fuel surcharges are the likeliest to be worth redeeming SKYPASS miles on, since you can take advantage of Korean's generous award chart without suffering the drawback of paying a high cash co-pay. On these low-fuel-surcharge routes you're likely to save money whether you choose to fly in economy, business, or first class.

For each airline I've given a sample route and the cost in SKYPASS miles for an economy ticket, and I've separated out the taxes and fees and the fuel surcharges. In all cases these prices are roundtrip, since Korean requires SkyTeam awards to be booked as roundtrips.

  • Delta to Peru, ATL-LIM. 50,000 SKYPASS miles, $103.40 in taxes and fees, $0 in fuel surcharges.
  • Delta to Japan, SEA-NRT. 80,000 SKYPASS miles, $80.04 in taxes and fees, $0 in fuel surcharges.
  • Aeroflot to Russia, JFK-SVO. 50,000 SKYPASS miles, $252.12 in taxes and fees, $0 in fuel surcharges.
  • China Eastern to China, LAX-PVG. 90,000 SKYPASS miles, $420.60 in taxes and fees, $8 in fuel surcharges.
  • China Airlines to Taiwan, HNL-TPE. 90,000 SKYPASS miles, $73.15 in taxes and fees, $0 in fuel surcharges.

Medium fuel surcharges

These routes charge less than $500 in fuel surcharges, and might be worth considering in premium cabins or if you find award space on dates with particularly expensive cash fares.

  • Delta to China, SEA-PEK. 90,000 SKYPASS miles, $70.60 in taxes and fees, $282 in fuel surcharges.
  • Delta to South Africa, ATL-JNB. 80,000 SKYPASS miles, $99.95 in taxes and fees, $390 in fuel surcharges.
  • China Southern to China, LAX-CAN. 90,000 SKYPASS miles, $70.60 in taxes and fees, $208 in fuel surcharges.

High fuel surcharges

These are the routes where high fuel surcharges mean economy award tickets are likely to cost the same or more than economy tickets, while premium cabin award tickets may cost the same as an economy ticket paid for with cash.

  • Delta to Europe, JFK-BCN. 50,000 SKYPASS miles, $81.25 in taxes and fees, $556 in fuel surcharges.
  • Air France to Europe, JFK-CDG. 50,000 SKYPASS miles, $113.16 in taxes and fees, $576 in fuel surcharges.
  • KLM to Europe, JFK-AMS. 50,000 SKYPASS miles, $82.26 in taxes and fees, $576 in fuel surcharges.

Those flights would cost just 80,000 SKYPASS miles roundtrip in business class, for a total cost of $1437.25 - $1489.16 if you value transferred Ultimate Rewards points at their cash value of 1 cent each. Unfortunately business class space on SkyTeam across the Atlantic is very poor so you're unlikely to be able to take much advantage of these price points.

Routing rules

The basic routing rules for SkyTeam awards are pretty simple, although there are a host of exceptions: you can have three segments in each direction between your origin and destination, one stopover per itinerary, and one open jaw at your destination (which does not consume your stopover).

Drew at Travel is Free wrote a more detailed guide to Korean's routing rules, but I don't know if there's much point in trying to intellectualize their rules and restrictions. Basically, you can do a lot of things, within reason, and you can do some things beyond reason,  if you use Korean-operated flights. For example, a LAX-PVG-NRT-PVG-JFK itinerary will not price out entirely on China Eastern, but if you make it LAX-PVG-NRT/NRT-ICN-JFK with the return operated by Korean, it'll happily price out. This may also have to do with a Maximum Permitted Mileage restriction — the point is there's no substitute for getting in and playing around with the search engine to see if it'll accept your particular crazy idea.

For example, the engine happily priced out LAX-HNL(stopover)-NRT(destination)-HNL(transfer)-LAX for 80,000 SKYPASS miles and $87.84 total in taxes, fees, and surcharges. While a roundtrip to Hawaii for 25,000 miles is a good deal, a roundtrip to Japan with a stopover in Hawaii for 80,000 miles is a great deal.

What I'm thinking about headed into 2017

Good morning from Portland, Oregon. If you're traveling for the holidays, I hope your flights are safe, comfortable, and on time and your roads are clear. As 2016 staggers towards a close it's natural for thoughts to turn to the new year. Here's what's on my mind.

Manufactured spend

Last week I read a post-mortem on 2016 that claimed manufactured spend was either dead or dying, and I assume there are parts of the country where that's more or less true. In other parts of the country the amount of spend you can manufacture is limited only by the time and attention you're willing to dedicate to the task.

As 2017 starts I'll be moving spend back to my Delta Platinum Business American Express to start running up the score on Medallion Qualifying Miles and towards a Medallion Qualifying Dollar waiver. I don't chase high-level Delta status anymore, but do enjoy the free checked bags and decent seat selection I get as a Delta Silver Medallion. The real reason I manufacture spend on that card, though, is the 1.4 SkyMiles per dollar I earn at the $25,000 and $50,000 spend levels. Since I value SkyMiles at more than 1.5 cents each, that's more valuable to me than putting the same spend on a 2.105% cash back card.

In the last couple months I loaded up on spend with my Chase Hyatt credit card in order to hit the $40,000 spend threshold, but my expectation is I won't be putting any spend on that card in 2017. The annual Category 1-4 free night award will still justify paying the annual fee, for now.

The biggest change to my manufactured spend practice is that thanks to some current opportunities I expect to spend much more time in drug stores and much less time in Walmarts in 2017.

Blogging

In the 2-and-change years I've been writing this blog, it's changed in a lot of ways. When I started I spent a lot of time documenting and describing the tips and tricks I was reading about on other blogs and FlyerTalk. As time went on I became more focused on exploring new opportunities and, as I put it, explaining "how things really work." Recently I've become more focused on optimizing strategies for particular goals, and I've become even more cynical (if that's possible) about the parasites who put their own interests above those of their readers.

I've lost some readers as my focus has shifted over the years, and I've also gained readers who appreciate my newer content more than the older. This blog will never be all things to all people, but it'll always be independent.

In 2017 I hope to write some more book and podcast reviews, since I read a lot and listen to a lot of podcasts, and I enjoy the opportunity to collect and distill my thoughts about them.

Subscribers-only Newsletters

In the last few months I've stepped up the tempo of the periodic Newsletters I send out to monthly blog subscribers. Partly that's because there's been a surge of new deals towards the end of this year, and partly it's because I enjoy the opportunity to write unconstrained from fear of "killing" somebody's favorite deal.

I'll always maintain this public blog because I think it's important to have as many unbiased voices available as possible as a counterweight to the mercenary affiliate bloggers flooding the internet. But deals and ideas that might be threatened by widespread exposure will continue to go in my Subscribers-only Newsletters.

And by the way, if you enjoy this blog I hope you'll consider supporting it with a monthly blog subscription in 2017!

Gambling

During the Great Financial Crisis, the federal government took the two main federal home loan insurers into conservatorship. For a range of technical and legal reasons, however, they did not force them into bankruptcy and did not wipe out the existing shareholders. And, strangely enough, those shares are still traded for just under $4 on the over-the-counter markets.

I think there's a non-trivial chance the new Administration will stop sweeping the GSE's profits into the Treasury, and those shares will become 10-100 times more valuable. So I bought some!

This isn't advice, just something I'm looking forward to in 2017.

Travel

2017 will be my year of Hyatt stays. After March 1, as a World of Hyatt Globalist I'll be eligible for suite upgrades on award stays. Plus, since I won't be trying to requalify as Globalist for 2018 I'll be free to redeem Hyatt points for all my stays and not be constrained by the availability of Points + Cash awards.

Already in the works are trips to Jamaica to stay at the Hyatt Zilara Rose Hall and to Lexington, Kentucky for the April races at Keeneland. Beyond that, the plan as always is to keep my eyes open for international travel opportunities, as well as shorter weekend trips domestically.

Things I have learned about booking Hyatt all-inclusive resorts

In the past few weeks I've gone from vaguely speculating about booking a winter weekend at a tropical all-inclusive resort to starting to plan an actual trip. Since, for good or ill, I'll be a Hyatt Gold Passport Diamond/World of Hyatt Globalist next year, I've been looking at Hyatt's all-inclusive properties. Here are a few things I've learned so far.

Standard award availability is very tight

At the Hyatt Zilara Rose Hall I happened to reserve the last standard room available over Presidents' Day Weekend, which is quite a few months from now.

At the Hyatt Zilara Rose Hall, the only room types bookable at the 25,000-point level are the "Hyatt Zilara King" and "Hyatt Zilara Double" room types.

Suite award availability may be a bit better

While there are no more standard room awards over Presidents' Day Weekend at the Hyatt Zilara Rose Hall, there are still suite night awards available.

According to the phone representative I spoke with, at the 40,000-point level I could still book the "Junior Suite King" room type.

The point is that even if you don't have any reason to book a suite, if you're willing to spend the additional points you should ask anyway, since you may have access to additional award space you wouldn't have if you insisted on booking a "standard" room award.

Since during peak times those rooms can be phenomenally expensive, you may still save money even when "overpaying" for suite night awards.

Cancellation policies are brutal

My award reservation at the Hyatt Zilara Rose Hall has a 45 day cancellation policy. That means in the first couple days of January I've got to decide whether I'll really make it to Jamaica in late February.

Feel free to book these awards speculatively, but also keep track of their cancellation policies and don't get caught paying some preposterous cancellation penalty for missing it by a day.

Hyatt Gold Passport Diamond point loans still apply

On a final note, it is possible for Hyatt Gold Passport Diamonds to book award nights without sufficient points in their account. This is a pretty cool feature which can be used for domestic and international award stays, and can also be used for all-inclusive award stays.

I am not ready to be seduced by Southwest

Now that I'm finally a short commuter train ride, rather than an inconvenient bus ride, away from a Southwest hub I assumed I'd be flying Southwest a lot more. After all, they offer a variety of nonstop flights around the country, Mexico, and the Caribbean, and when "Wanna Get Away" fares are available Ultimate Rewards points are worth more transferred to Southwest than when redeemed for paid flights on other carriers.

But it turns out I still don't fly Southwest, for excruciatingly simple reasons.

Southwest doesn't participate in — or have their own — decent search engines

ITA Matrix is kind of primitive, and I understand that Google is trying to encourage people to use Google Flights instead. But both search engines are great! You can use ITA Matrix to produce a list of flights that correspond to criteria you specify in advance, and you can use Google Flights to alter your search on-the-fly to dial in the airlines, dates, and airports you want to search. Two great tastes that taste great together.

By forcing you to use their own garbage search engine every time you want to find a Southwest flight, Southwest increases by 50-100% the amount of work necessary to compare all the relevant flight options.

Why do I say the search engine is garbage? Here are a few things you can't do using Southwest's search engine:

  • Specify non-stop flights;
  • Specify flexible dates;
  • Specify specific fare classes.

Each of one these requires you to wait for search results to load, and reload, and reload, and reload, while they can all be specified in advance using ITA Matrix or specified on-the-fly with Google Flights.

Southwest is not a low-cost carrier, it's just inconvenient

The reason I've got Southwest on the brain is that I'm trying to plan a Caribbean getaway for early next year and I keep thinking, "I should check Southwest flights." Then I check Southwest flights and get frustrated that I'm wasting my time.

Here's Southwest's one daily non-stop flight from Baltimore to Montego Bay, Jamaica, over Presidents' Day weekend:

And here are two perfectly good American flights (with a connection):

The question to me isn't whether the Southwest flight is "better" or "worse" than the American flights, it's whether the Southwest flight is going to be better by enough, often enough, to justify jumping through their hoops in addition to the ordinary searches I do for paid tickets and awards on real airlines.

Booking Southwest flights can be worth it, but you've got to commit to shenanigans

I don't want to cast aspersions on the judgment of readers who decide that Southwest is the right airline for them. But if you do decide to make Southwest part of your life, there are two important things to keep in mind.

First, always book tickets out of funds in your Southwest account. Most fixed-value rewards currencies can be used to book Southwest tickets in every fare class except "Wanna Get Away" fares. But since Southwest tickets can be freely redeposited into your account and reused, you can apply the credit from your high-value ticket redemptions to cheap Wanna Get Away fares. That means 20,000 Flexpoints can be redeemed for any $399 Anytime fare and that $399 fare can be used to book 2 $200 Wanna Get Away Fares. This is one of the key benefits of Southwest and if you're not using it you're likely leaving money on the table.

Second, consider chasing a Companion Pass. While plenty of affiliate bloggers will tell you how easy it is to earn with Chase credit card signup bonuses, it's also easy to earn through every other method of travel hacking: shopping portals, reselling, manufactured spend, and of course actually booking paid tickets. By doubling the value of your Rapid Rewards points and doubling the value of the funds in your Southwest account, a companion pass can legitimately bring down the cost of Southwest tickets enough to offset the inconvenience of being seated in a cattle car (not that I'm biased).

Conclusion

My older brother is a Southwest enthusiast. He got into travel hacking for the sole and exclusive purpose of getting a Southwest Companion Pass, and he took full advantage of it for 4 years as he got married and had kids. He was sure to check in 24 hours before each flight to get the lowest boarding number. And now that his last year with a Companion Pass has lapsed he's always complaining about how much flights cost.

And that's basically my point: Southwest isn't a low-cost carrier, and it doesn't have any particular advantage in convenience or comfort. It's a lifestyle, and there are a lot of people who are enthusiastic about that lifestyle.

I just don't think I'm ready to become one of them.

Liquidating tiny-denomination prepaid debit cards

If you read yesterday's post and rushed out to buy up a slew of 5% Back Visa Simon Giftcards, and then triggered 5% cash back on each of them, you are probably feeling pretty good about yourself.

You're also probably realizing that you've got a drawer full of $25 Visa debit cards, and may need some suggestions for liquidating them. I'm here to help.

Buy gift credit

If there's a particular world-swallowing online merchant you do a lot of shopping with, you can simply use your $25 debit cards to reload your gift card balance.

This goes for any merchant where you have a consolidated or well-organized method of keeping track of gift credit — Uber and Starbucks spring to mind, with their beloved smartphone apps.

If you are buying gift credit at a merchant where you already reliably spend money, this is a good way to convert prepaid debit cards into cash savings, as long as your swollen gift card balance doesn't make you spend more money than you otherwise would have.

Pay bills

I don't personally have very many bills, but I'm assured by experts that most people have a great many bills. They might be:

  • Phone;
  • Internet;
  • Cable;
  • Walker (dog, cat);
  • Insurance (homeowner's, renter's, car, health, dental, long-term care, yacht, RV, flood, drought);
  • Utilities (electric, gas, hot water, cold water, lukewarm water, elevator, heating oil, cooling oil).

Some of them may accept debit card payments at face value. Even if you usually make these payments quarterly or annually, you may be able to prepay them and have the balance roll over from one billing cycle to another.

This is a basically excellent idea, but like buying gift credit, you will quickly run into problems when you're producing more $25 Visa debit cards than you need to cover even your most speculative bill payments.

Liquidate as usual

Of course, these are PIN-enabled Visa prepaid debit cards, so it's also perfectly possible to liquidate their (small) balances as usual: by buying money orders or making bill payments at any merchant that allows those services to be paid for with PIN-enabled debit cards.

The problem with this approach is that while it's likely to be the cheapest in out-of-pocket cost, it's likely to be the most expensive in opportunity cost, because the same trips could be used to liquidate higher-denomination (and more profitable) PIN-enabled debit cards instead. This is the issue I've referred to in the past as "liquidation bandwidth."

If your local merchants don't throttle payments, that may not be an issue for you: you can liquidate these tiny-denomination cards side-by-side with higher-denomination cards. But if you're limited to 4 debit card swipes, or a single swipe, then you'll likely be better off swiping a higher-denomination, rather than lower-denomination, card.

Pay up

It's not nearly as sexy as loading up a Starbucks card or settling a decade's worth of car insurance payments, but there are also ways to simply pay to liquidate small-denomination debit cards. You can pay many kinds of bills online using Plastiq at a cost of 2.5% (61 cents on a $24.39 payment).

If you enroll using my personal referral link you also earn "Fee-free dollars" which allow you to make eligible bill payments without paying any fees at all — I get 400 fee-free dollars (16 $25 cards!) and you get 200 fee-free dollars (8 $25 cards!).

Plastiq has one key advantage over other bill payment services for liquidating these tiny-denomination cards: it doesn't have a minimum fee. When liquidating high-denomination cards the objective is to have a low, flat fee. That's one reason online quarterly tax payments are popular — at least among self-employed bloggers who have to make online quarterly tax payments anyway!

On the other hand, when liquidating low- or tiny-denomination cards, it's much preferable to have a fixed percentage fee no matter how high it is.

Conclusion

The good news is that 5% Back gift cards are capable of producing almost pure profit, no matter how much you have to pay to liquidate their residual balances.

The bad news is that once you have a stack of cards with residual balances, you really should put in a little bit of time to figure out the cheapest, most efficient way of liquidating those balances back to cold hard cash.