Optimizing Hilton points and nights earning across cards

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In general, I prefer the American Express Hilton HHonors Surpass to the Citi Hilton HHonors Reserve. To review, the American Express card's three big advantages are:

  • issuance by American Express, so the primary user's card and all authorized users are eligible for American Express Offers for You;
  • Better bonus categories (gas and grocery versus airline and car rental) and higher earning in bonus categories (6 HHonors points instead of 5);
  • Lower annual fee ($75 instead of $95).

Both cards grant Diamond elite status after $40,000 in purchases each calendar year.

The comparison isn't completely one-sided, however. In addition to the fact that some people have success making payments against Citi credit card accounts over the phone using debit cards, the Citi Hilton HHonors Reserve card also grants an annual weekend night certificate each cardmember year you spend $10,000 or more with the card.

What's the imputed redemption value of a free weekend night?

Since the card earns 3 HHonors points on purchases outside of bonus categories, we can find the imputed redemption value of the annual free night certificate by comparing it to earning 6 HHonors points per dollar at grocery stores or gas stations with the Surpass card. Assuming you value HHonors points earned with the Surpass card at precisely their imputed redemption value (0.35 cents each), you have to get at least $105.25 in value from the free night certificate in order to justify earning it instead of 30,000 additional HHonors points or $210.50 in Arrival+ miles.

That is relatively easy. There are only 3 Hilton HHonors price points (5,000, 10,000, and 20,000) lower than 30,000 and 7 HHonors price points at 30,000 or above. That would imply that under most circumstances, if you value HHonors point enough to earn them in the first place, it's worth carrying the Citi Hilton HHonors Reserve card.

Keep in mind how imputed redemption values work: they show the breakeven point that justifies earning hotel points instead of cash back, not the actual value of the points when redeemed. The more value you typically get from your HHonors points above and beyond their imputed redemption value, the higher the value you need to place on the free night certificate to justify earning it instead.

And then there's the annual fee

If the Citi HHonors Reserve card didn't have an annual fee, the analysis would end there — the free night certificates would be so valuable it would be worth carrying multiple copies of the card and earning as many free nights as possible.

But there is an annual fee, and not a cheap one. Adding back in the $95 annual fee raises the breakeven imputed redemption value from $105 to $200, the equivalent not of a 30,000-HHonors-point hotel redemption, but a 60,000-point one!

That leaves the free weekend night certificates competitive with HHonors point redemptions at many high-end properties, but it makes them much less competitive with the typical mid-tier urban properties I stay at.

And of course weekend night certificates can only be redeemed over the weekend. That doesn't radically reduce the value for me (since I like taking trips over the weekend), but it's something to keep in mind.

Conclusion

The Citi Hilton HHonors Reserve card can provide a value competitive with the American Express Hilton HHonors Surpass card under two conditions:

  • during the first year, thanks to its signup bonus of 2 free weekend night certificates and a $100 statement credit;
  • and during subsequent years, if the cardholder has a plan to work the free weekend night certificate into a redemption at Hilton properties costing 60,000 or more HHonors points per night.

Of course, if you can talk Citi into waiving the annual fee in subsequent years, the value proposition reverts to the first one I outlined above.

Otherwise, the Surpass card's increased earning rate in lucrative categories makes it my go-to card for manufacturing HHonors points.

I am not addicted to Amazon

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Earlier today I pooh-poohed the Chase Freedom's earning of 5 Ultimate Rewards points per dollar spent at Amazon.com in the 4th quarter of 2015. While I do make purchases at Amazon.com occasionally, especially since I generate a small amount of Amazon gift credit each month using Amazon Allowance and microhacking, I don't consider myself a regular Amazon shopper. Since I know many of my readers are, I thought I might as well explain why.

"Free" shipping is now standard almost everywhere online

Obviously shipping is a cost of doing business for any online merchant selling physical goods, so it's not clear in what sense shipping can be "free:" it's included in the prices of the goods you order for delivery.

On the other hand, the included shipping that's now standard in online pricing makes those prices easy to compare, where they hadn't always been in the past, when Amazon first started offering free shipping on orders for their Prime members.

Amazon only occasionally has the best prices

To qualify for free shipping, orders have to be either sold or fulfilled by Amazon (although of course some Amazon Marketplace sellers also include shipping to compete more effectively with Fulfillment by Amazon sellers).

Here are some things I've purchased online in the last few months:

  • Dockers trousers. $35 on Amazon.com, $35 on Dockers.com;
  • Culligan Filter Replacement Cartridge. $12.67 on Amazon.com, $14.99 on Culligan.com;
  • Mr. Coffee 12-Cup Replacement Decanter. $10.97 on Amazon.com, $7.99 on Ebay.com.

In other words, sometimes Amazon is the same price as other merchants, sometimes it's more expensive, and sometimes it's cheaper. There's no inherent savings when shopping on Amazon.com.

Amazon restricts portal cash back

Last year I wrote that I was pleasantly surprised to earn cash back shopping at Amazon.com after clicking through TopCashBack, since at the time Amazon was paying 8% cash back for purchases in their "Men's Fashion" department, which happened to be where I was shopping.

The flip side of that is that Amazon regularly changes which departments earn portal cash back ("Star Wars Toys" is a current cash back category).

Actual online merchants like Dockers.com tend to have relatively stable, relatively high payouts: currently 5% cash back through Discover Deals, which rises to 10% cash back if you enrolled in time for the current 12-month double cash back deal.

Conclusion

Thanks to our brothers in the reselling game, every travel hacker has at least a general idea of how cash back portals can save money on actual purchases of physical goods. What they may not realize is that those portals can bring prices down well below the supposed savings offered by Amazon. Even better, sites like evreward and Cashback Monitor make it easy to compare the relative payouts from a wide range of shopping portals.

So by all means, shop at Amazon. But it's always worth a quick glance to find out whether you can save more money at one of the thousands of online merchants Amazon is competing against.

Thinking about ethics in travel hacking

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I spent this past weekend in Austin hanging out with a friend who's heavily involved in travel hacking, and he mentioned a few techniques that he had used to manufacture spend, about which he was embarrassed since they seemed unethical to him.

Everyone has different things they’re wiling and unwilling to do, so I don’t blame him for observing different ethical lines than I do. But I also think it’s useful to interrogate why certain activities seem more or less ethical to different people.

Breaking the law is illegal

The clearest cases are when a technique is illegal. With the exception of laws that are themselves unethical, I believe most people, most of the time, in democracies have an duty to obey the law, and in exchange receive the protection of the law.

For example, since structuring transactions to avoid reporting requirements is illegal, and the law against it is basically reasonable, you shouldn’t structure transactions.

Program rules are often written elliptically

Here’s a thought experiment. Delta SkyMiles can be redeemed for passengers besides the account holder. So let’s say your grandfather redeems his SkyMiles for an award ticket for you, then passes away. The ticket is still valid, and I think virtually anyone would have a clear conscience flying on the ticket that had been “purchased” with their living (since deceased) grandfather’s SkyMiles.

But if the account has been closed, I don’t believe it would allow any changes to be made to the award ticket, since Delta’s system treats award changes as first a redeposit of the miles, then a new redemption. Just in case you need to make changes to the ticket, I would find it reasonable to delay notifying Delta that your grandfather had passed. After all, the ticket was purchased prior to your grandfather’s death, so we’ve already established that these are “guilt-free” miles — why shouldn’t you be allowed to use them?

But if you’re willing to keep your grandfather’s account open until your existing reservations have been completed, it’s a short hop to keeping the account open until his existing SkyMiles have all been redeemed for new reservations. If he earned the miles in good faith and gave you access to his SkyMiles account, then what could be unethical about using the miles he accumulated?

Why should you ever notify Delta that your grandfather is no longer with us?

Here's the relevant rule from Delta's online membership guide:

"Under the SkyMiles Mileage Expiration policy, miles do not expire. Delta reserves the right to deactivate or close an account under the following circumstances:

  • A member is deceased"

In other words, it's up to Delta to cancel your grandfather's SkyMiles account. This is sometimes sloppily referred to as miles "expiring when you do," but that's overstating the case. According to the published rules, miles don't expire. However, Delta reserves the right to deactivate or close dead members' accounts.

Whose responsibility?

The terms and conditions of every credit card I know of states that the purchase of cash equivalents is not eligible rewards-earning activity (although FIA Card Services recently send me a letter telling me I could buy lottery tickets with my Fidelity Investment Rewards American Express). And yet almost all cash equivalent purchases do, in fact, earn rewards. Is earning rewards in that manner unethical?

The key question for me is who carries the responsibility for the enforcement of the agreement. Remember that the credit card contracts you agreed to don’t prohibit the purchase of cash equivalents — they simply say that such purchases won’t earn rewards. Since the credit card companies are the ones running the rewards program, they are also perfectly situated to enforce that clause of the agreement.

In the thought experiment above, Delta can’t be expected to know whether its SkyMiles members are alive or dead. But in the case of the purchase of cash equivalents, the purchase is being run on the credit card’s payment network, being processed by the credit card company, and then being deemed eligible for rewards by the credit card’s rewards program. The customer is making a purchase that is not forbidden by the credit card agreement’s terms.

In other words, if it’s ethical to buy cash equivalents, I don't see how you can have an affirmative duty to notify your credit card company each time they erroneously grant rewards for the purchases.

Conclusion: find the right shade of gray for you

Unfortunately, the vast majority of the techniques we use fall into the vast gray area between the flagrantly illegal and the uncontroversial. If you make a purchase with a credit card, then return the goods for cash, is that ethical or unethical? Does it make a difference if you did so intentionally? How much of a difference? If you return something purchased through a shopping portal and are allowed to keep the points, is that ethical or unethical? If you do so intentionally, on a large scale, after being warned not to, you may end up with date with a US Attorney in Seattle.

Fortunately, man is a morally calculating animal, so the answers to those questions (and more!) are available to anyone willing to think about them.

On the other hand, there’s no guarantee we’ll arrive at the same conclusion!

That’s why the decision of what techniques to use is an essentially personal one. We can try to reason our way through these questions, separately and together, but at the end of the day the only advice that matters is not to do anything that you consider unethical, and try to give everyone else the benefit of the doubt that they’re doing their best to behave ethically as well.

Breaking: Hotel IT is not very good

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One reason I love meeting travel hackers is that every one has a unique "origin story" for how they became interested in the game in the first place. For example, I accidentally earned elite status with Delta one year, and in the course of searching out the benefits of my Silver Medallion status began to learn about and get involved in the community, as well.

Often an initiation into travel hacking comes with the discovery of a new trick. A friend discovered that his United global upgrade certificates weren't actually disappearing from his account when he redeemed them. He was sure no one else on Earth could possibly know about this bug (I believe it was actually quite widely known among travel hackers who fly United).

Hotel loyalty programs have pretty bad IT

In many ways this is understandable: Hilton HHonors has to design systems that allow both the Hilton Garden Inn DFW Airport South and Conrad Maldives Rangali Island to interact with Hilton's sprawling reservation system — and Hilton doesn't even own most of the properties using their software!

Sometimes bad IT just makes interacting with the chain more of a nuisance — IHG Rewards turns something as simple as signing up for a promotion into a Herculean achievement, and Hyatt doesn't allow award stays to be changed or canceled online.

But at other times, bad hotel loyalty software design can be turned to your advantage. Here are a few questions you might ask as you make your way through the world of hotel loyalty programs. 

How do hotels batch nights into stays?

Every hotel loyalty program I'm aware of "batches" consecutive nights at the same property into a single stay for the purposes of earning elite status and qualifying for promotions. For example, pre-devaluation a single Club Carlson credit cardholder couldn't book multiple pairs of award nights and receive every other night free. For stays longer than 2 nights, people developed workarounds like having a spouse book every other pair of nights, or booking the first two and last two nights before booking a fifth night connecting them to receive 5 nights for the price of 3.

Another workaround was to simply pay cash for a third night, which gave you the added flexibility to make your cash reservation for either the first or last night — whichever was cheaper. In one of my very first subscribers-only newsletters, I shared my experience doing so during a promotion that gave 38,000 bonus Gold Points after 3 paid stays. Even though only one of my 3 nights was paid, my theory was that since my first night was paid, when the two reservations were batched together all three nights were treated as paid nights and I earned the bonus Gold Points — enough points to cover the entire 2-night award reservation!

I don't know how other loyalty programs batch nights into stays — but I'd like to find out.

How do hotels determine if a stay is eligible or not?

Marriott has recently run a series of promotions where bonus points are earned starting on your second eligible stay with Marriott. Besides being another example of how poorly Marriott Rewards treats its members, it also raises the question of how Marriott determines if a stay is eligible or not. After all, even if you stay with Marriott frequently, you want to start earning those double points as soon as possible. It may be that Marriott requires you to stay on a paid rate. It may be that Marriott will treat stays as eligible if you simply charge a movie or a beer to your room on an award stay.

I don't know how Marriott determines if stays are eligible — but I'd like to find out.

Peak under the hood whenever possible

I hope you're already logging into your hotel loyalty accounts after your stays are completed in order to make sure you received your earned points. Instead of just making sure stays appear, you should also do your best to understand why you earned the exact number of points you did. One of the reasons I developed my points density charts is precisely how difficult the chains make it to determine how they award points.

For example, Hilton awards 10 "base points" per dollar spent. If you select the "Points & Points" earning style, you earn a 50% bonus on those base points. If you're a Diamond elite, you earn another 50% bonus, but only on those base points, not the Points & Points bonus points. In other words, Diamond elites earn 20 HHonors points per dollar spent at Hilton properties — plus 1,000 extra bonus points at many Hilton brands!

Conclusion

In many ways these are the same kinds of questions we ask about airline loyalty programs (if I'm rebooked on an award ticket into a paid fare class, will I earn miles? Can I apply upgrades?) and manufactured spend (are these debit cards PIN-able?).

On the other hand, hotel loyalty programs are different in that consolidation has been much more gradual than what we've seen in the airline industry and that hotels are, by and large, not owned by the chains that administer their loyalty programs. Meanwhile, hotels constitute a large part of my travel budget; as I sometimes point out, I only need one or two plane tickets, but I might need 5 or 10 nights in a hotel.

That increases my incentive to be more aggressive with hotel loyalty programs than I am with airlines — I often simply pay whatever the airlines are asking for, but almost never stay at hotels on paid rates.

Taking a manufactured spend inventory

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Last week I wrote that — unless you're a reimbursed business traveler — your best bet for earning as much travel as possible, as cheaply as possible, is to manufacture spend furiously. Actual purchases made for consumption by a credit cardholder won't generally earn sufficient miles and points to pay for a single trip, let alone an entire travel hacking lifestyle.

That's the origin of my maxim that miles and points earned from everyday spend should be a rounding error in your travel hacking strategy. You may as well be paying with cash.

With that in mind, I thought it might be worth laying out a few suggestions for what it means to manufacture spend furiously.

Reflect often, but not too often

I'm a blogger, so I don't mind spending hours poring through forums and blog comment sections finding opportunities that aren't widely known, so I can share them with my readers and in my subscribers-only newsletters.

It's literally my job.

But it's not your job. You're a lawyer, consultant, software developer, marketing professional, or exotic dancer. You have a family. You shouldn't be spending every spare minute researching new manufactured spend techniques.

But you should spend the occasional minute examining the techniques you have available, and making sure you're maximizing them.

Are you earning the miles you use, and using the miles you earn?

If you spent any time following affiliate bloggers before discovering my blog, you may have signed up for a variety of random credit cards you don't actually use to manufacture spend. In that case, you might be sitting on 100,000 Membership Rewards points, 80,000 Marriott Rewards points, or 50,000 Delta SkyMiles.

Do you have plans to use them? Can you work them into your actual travel plans?

Don't waste your time applying for cards that earn miles and points you can't use, and make sure to use the miles and points you do earn.

The corollary is that lower signup bonuses and earning rates can be worth pursuing if they're the miles and points you're actually going to use. If you aggressively redeem American Airlines AAdvantage miles during the "low" season to Europe, 40,000 AAdvantage miles are worth a lot more than 60,000 or more Delta SkyMiles.

9 questions about your manufactured spend practice

I don't repeat myself here on the blog much because I find it excruciatingly boring to write the same things over and over again. With that in mind, here are 9 questions to ask while taking your personal manufactured spend inventory:

Conclusion

I hope I've made clear that I don't believe everyone should be pursuing every possible technique as aggressively as possible. There will always be techniques that are too time-consuming, or that simply require more attention than you're willing to pay, to be worth your time and attention.

But once in a while, even the most time- and attention-constrained travel hacker should take a quick inventory to make sure that the time and attention they do have is being deployed in the way they earns them the trips they want to take — hopefully as cheaply as possible!

Do this now: register for IHG fall promotion

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Between September 1 and December 31, 2015, IHG is awarding a range of points for completing a targeted set of offers. Here are the offers I was targeted for:

Without applying for the IHG Rewards Club Select Credit Card, I could complete the rest of my offers with two, 3-night stays at Holiday Inn hotels (including at least one weekend) and earn a total of 48,000 bonus IHG Rewards points.

If you like the IHG Rewards Club program and have two 3-night stays planned during the promotional period, this promotion might make it worth directing those stays towards Holiday Inn properties.

Personally, I consider IHG Rewards Club to be tied with Marriott in the category of "worst hotel loyalty program," so I won't be participating.

Either way, you should still register now, before you forget.

Manufacture spend furiously

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Yesterday Miles Per Day reported that US Bank Visa Buxx cards, which have been closed to new applicants for many months but have continued to work in the interim for existing cardholders, will no longer be loadable with new funds after October 24, 2015.

These cards are terrific, especially if you have access to US Bank ATM's, which allow free withdrawals of the $2,000 that can be loaded monthly to each card at a total cost of $10. If you used a card like the Barclaycard Arrival+ MasterCard, you could earn $40 in statement credits, per card, against travel purchases each month.

In other words, each US Bank Visa Buxx card you carried allowed you to purchase $480 in annual travel at a 75% discount.

I like small, isolated techniques

On the one hand, $480 in annual travel reimbursements is small fry compared to many other available techniques. But what I like about US Bank Visa Buxx cards is that the tool is isolated from all my other manufactured spend techniques: if you have access to US Bank ATM's, you don't need to cannibalize the liquidation bandwidth you're using with any other technique. It's $2,000 in "extra" manufactured spend per month — and cheap, too!

I do everything I can

Obviously, I don't use manufactured spend techniques I don't have access to (I sometimes hear from readers who can still buy Vanilla Reload Network cards!), and I don't use manufactured spend techniques I don't know about.

But to the extent possible, I pursue every avenue of manufactured spend available, because it's impossible to know when any particular technique will cease to be available. Since I do my best to redeem rewards currencies roughly as quickly as I earn them, I never want to find myself with empty account balances and no way forward to earn more.

Two ways to travel exclusively on miles and points

There are two ways to generate enough miles and points to fund the number of trips I want to take at deep enough discounts to make them affordable: be reimbursed by an employer for frequent business travel, or manufacture spend furiously.

While my takeaway from my point density charts is that paid hotel stays are an incredibly inefficient means of generating sufficient points for award stays, that only holds if you're paying for your own stays. A Starwood Preferred Guest elite paying for stays with the American Express co-branded credit card earns 5 Starpoints per dollar spent at Starwood properties, and would have to spend $2,000 on paid stays before they earned enough points for a single award night at a mid-tier property.

I don't think I've spent $2,000 on hotel stays in my entire life to date.

On the other hand, a Starwood Preferred Guest elite paying for stays with their co-branded credit card and being reimbursed by their employer for those stays wouldn't have to pay a penny for an award night at a mid-tier property; they'd just have to wait until their employer had spent $2,000 on their behalf.

Meanwhile, the same 10,000 Starpoints would cost someone manufacturing spend with their co-branded credit card perhaps $86 in fees, depending on the techniques used.

Manufacture spend furiously

If your reimbursed business trips generate enough miles and points to finance all the travel you're interested in, you're in luck.

Otherwise, you can research every technique you come across to find out whether it can be integrated into your miles and points strategy.

The stories affiliate bloggers tell about paying for travel with signup bonuses are "just so" stories, which is why I don't tell them. Of course if you work backwards from the signup bonus you're trying to sell, you can find trips that will be exactly covered by the points earned. But if you want to be in charge of your own miles and points strategy, rather than running off to the Maldives every time an affiliate blogger tells you to, you should be pursuing a robust, diverse miles-and-points-earning strategy.

And unless you're one of the lucky few, frequent business travelers, that strategy should include as many different manufactured spending techniques as possible.

Travel hacking when you've got plenty of money

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Before I learned the first thing about travel hacking, I still traveled, and I was still broke. So for me, travel hacking straightforwardly allowed me to take the trips I was already taking — and more! — while paying far less out of pocket than I had been when all my trips were paid for with cash.

I don't have to fly Spirit anymore, either.

That sometimes leads to some crossed wires between me and my readers, since on the one hand I don't pursue "aspirational" redemptions with the same fervor (the Maldives are expensive!), but on the other hand I have much more time to spend earning miles and points every day than prominent bankruptcy attorneys do.

But that doesn't mean I actually believe travel hacking is just for poor people! In fact, there are some opportunities that are either exclusively available to, or more lucrative for, people with plenty of assets to sink into them. Here are three opportunities I'd pursue if I had a few hundred thousand spare dollars lying around.

Brokerage bonuses

Perhaps the only links on my site that haven't changed in the years I've been blogging are those to Fidelity's United, Delta, and American brokerage bonuses. Deposit $100,000 for 9 months, earn 50,000 miles.

You're eligible for one bonus every rolling 12-month period.

Note that you shouldn't do this if you're going to let a Fidelity salesperson talk you into an expensive, actively managed fund. But if you are willing to put in the effort to coordinate your Fidelity account with your other cash and assets, these miles can be very close to free.

The next-lowest hanging fruit here may be Scottrade, which currently offers tiered bonuses up to $2,000 for deposits of $1,000,000. As a percentage return, you're best off depositing just $200,000, however, and earning a $600 bonus.

See Doctor of Credit's list of current bank account bonuses for some other opportunities available to the well-heeled.

Bank of America Preferred Rewards

With a cumulative $100,000 on deposit in Bank of America, Merrill Edge, and Merrill Lynch accounts, you qualify for Bank of America Preferred Rewards Platinum Honors, which has one key benefit: a 75% bonus on rewards earned with the BankAmericard Travel Rewards credit card. Since the card earns 1.5 cents per dollar spent everywhere, the 75% bonus makes it a 2.625% cash back card, when redeemed against travel purchases made with the card.

That's the best return you're going to get on a Visa or MasterCard for purchases everywhere (the Discover it Miles card gives 3% cash back everywhere for the first year of card membership).

Kiva Loans

I've left the Kiva loan business for two reasons: first, my PayPal accounts have all been closed! But second, I couldn't justify tying up money in months-long Kiva loans when the same money could be turned over weekly at my local merchants, albeit with far higher transaction fees.

With access to much more liquidity but finite local avenues for manufacturing spend, I'd be thrilled to pour that additional liquidity into Kiva loans using super-lucrative US Bank credit cards.

Conclusion

Fortunately, virtually all manufactured spend and travel hacking techniques are available regardless of your income, let alone your net worth, as long as your credit score and income get you approved for the credit cards you want. I'm living proof of that.

But there are advantages to having a few hundred thousand dollars to throw around, as well. This is America, after all!