Use these 3 weird programs to search Star Alliance award space

In Chapter 5 of my occasionally-selling ebook, I discussed the technique of using All Nippon Airways' search tool to find Star Alliance award space. Recently, they made some changes to their award search function which makes it somewhat less convenient to use while searching for Star Alliance award space.

But it's still relatively easy to find partner award seats if you know where to look.

Step 1: United Mileage Plus

United Airlines is a US-based airline, which means most readers likely already have a Mileage Plus account. Log in, then search for a one-way or roundtrip award flight from your origin to destination and see what United comes up with.

Step 2: Air Canada Aeroplan

Air Canada's Aeroplan frequent flyer program has online access to partner award space on airlines that United Mileage Plus doesn't. It's slightly difficult to find their online award search tool, but just log into Aeroplan and visit this URL to get started.

Step 3: All Nippon Airlines

All Nippon Airlines has made some odd reconfigurations of their website which makes it harder, but not impossible, to search across the entire Star Alliance. You can now only search roundtrip or multi-city flights.

Once you log into your account, you can search for roundtrip or multi-city flights between any Star Alliance cities. In other words, once you find an arbitrary city pair with Star Alliance availability, you can search for availability between any other other Star Alliance cities by inputting the existing availability as the "first" or "second" leg.

Then you should be able to call and book the Star Alliance availability using whichever program you happen to have your mileage balances with.

Conclusion

You don't normally have to use every technique for every award booking you make; often, the first search you make will simply throw up the award seats you need. But when it doesn't, make sure you've exhausted every possibility before you consider paying cash for your seats.

Use Hipmunk to find positioning flights

There are a lot of websites you can use to search for paid flights. Kayak is one of the most popular, but Orbitz, Expedia and Priceline will all find you tickets as well. If you're booking paid flights with Ultimate Rewards points you'll need to use their internal search engine, and the same is true of US Bank Flexpoints.

All those sites work, and they all have roughly similar search features: you can search for specific dates or flexible dates, you can specify your cabin of service, and you can filter by airline and time of day.

What none of them let you do is filter by different times of day depending on the day of the flight. Let me explain.

Award availability often requires positioning flights before or after the award segments

Award availability is the aspect of travel hacking that we have the least control over. Whether or not an airline makes seats available on the dates we need them is entirely at the discretion of the airline. While much digital ink has been spilled over the best ways to find award seats, ultimately it's not something we can predict in a reliable way.

Further, when award availability does become available, it may not exactly suit our needs. There may be award seats from an alliance hub city, but not on flights from your home airport to the hub. If you're committed to booking the award seats, that means you'll need a positioning flight: either a paid flight or an award on a different carrier that gets you to the airport in time to take your award flight.

Of course, positioning flights can be necessary at the beginning or end of a trip.

Use Hipmunk to find positioning flights

When you search for flights with every other search engine I know of, you can filter by time of departure, but that filter applies to every day searched. For example, on ITA Matrix filtering by "early morning" departures returns early morning departures for every day within the search range:

HIpmunk is the only flight search engine I know of that lets you filter by departure times across day boundaries. For example, I have an upcoming award flight booked on Air Berlin between Berlin and New York City. But I don't live in New York City, and there's no oneworld award space between New York City and my hometown, which means I need a positioning flight.

Since we don't want to go into the city (we'll be getting back from 17 days in Europe), I'd like to search for the cheapest flight that leaves either the evening we arrive in New York or the next morning. In other words, I'm fine staying overnight at the airport if it saves us some money, but I'm not willing to wait to fly out until the next evening.

Lo and behold, Hipmunk found me the perfect flight:

We'll stay overnight at JFK, leave early the next morning, and be back home early that afternoon.

"Pop Finance" is a pretty good book

This is a review of "Pop Finance," by Brooke Harrington. You can find all my previous book reviews here. If you're interested in buying a copy, I hope you consider using my Amazon Associates referral link.

I first heard about "investment clubs" from my Italian immigrant barber back in New England. He and some of his business associates and cronies get together once a month and contribute a nominal sum to a common pot. They then vote on which stocks to buy with that month's contributions.

My barber seemed to realize that this was a strange way to invest in the stock market, but explained that the real point wasn't necessarily to pick winning stocks, but as a forced savings vehicle: if you wanted to hang out with your buddies, you needed to find $50 to save each month, which was enough incentive to get people to save money who otherwise wouldn't bother.

With that in mind, I was excited to stumble across "Pop Finance," an ethnography of investment clubs in the San Francisco Bay Area written by Brooke Harrington. The principle research behind the book was conducted over the course of 1998 — in other words, at the peak of the 1990's tech bubble — with followup research in 2004, in the midst of the Bush Administration stock market doldrums.

Mass participation in the stock market is something that requires explanation

Today, popular ownership of publicly-traded shares, either individually or through mutual funds, is so common that it seems part of the natural order of American economic life. So it's worth pointing out that this isn't the only way that it's possible to save money, whether for retirement, health care, or educational expenses.

To this day, it's perfectly legal to simply save half your salary from age 25 to age 65 in FDIC-insured vehicles like savings accounts and certificates of deposit that earn market interest rates on the money saved. That volume of savings would allow you to then continue spending the same amount of money (half your lifetime salary) from age 65 to age 105, with a little left over depending on where market interest rates happen to fall during your lifetime.

Of course, Social Security exists, so you don't need to replace your entire annual consumption through savings — Social Security will replace 18-90% of your income (depending on your lifetime earnings), so you only need to replace the remaining portion, meaning you can spend more than 50% of your income and still spend the same amount during your working life and your retired years.

A private pension replacing even more of your income would mean even less savings would be required to smooth out your consumption over your entire lifetime.

Harrington convincingly argues that mass participation in the stock market, in her case in the form of investment clubs, was the result of two factors that made the above logic fall apart in the 1990's:

  • Corporate defined benefit pensions were replaced with defined contribution plans, often self-directed and invested in stocks and bonds;
  • Between 1985 and 1995, real wages declined while corporate profits tripled. In other words, for the average American, saving half their salary in FDIC-insured savings vehicles would mean a decline in living standards in retirement, while purchasing "the market" would mean an increase in living standards in retirement, or even early retirement.

Finally, I'll add that obviously the overwhelming majority of Americans today are incapable of or unwilling to live on half their salary. There are many reasons for this: status anxiety, a feeling that they've "earned" the right to enjoy their money, and of course in the case of prosperous coastal cities, the accelerating cost of living.

Ultimately, that means either settling for a much lower standard of living in retirement, or investing in riskier assets with a higher potential rate of return than FDIC-insured savings vehicles.

Day trading is a very intuitive way to invest in the stock market

Once you've decided that the stock market is the only way to secure the lifestyle you envision for yourself in retirement, day trading is the obvious method of doing so: since different stocks move in different directions on a daily basis, by buying stocks before they go up, and selling them before they go down, you can earn more on a daily basis than in a whole year of FDIC-insured interest.

In fact, if your wins are big enough and your losses are small enough, you don't even need to be right a majority of the time! After all, one 10% gain offsets four 2% losses with 2% left over as your profit, not annually, but daily!

Investment clubs are day trading by committee

Investment clubs, like day traders, also purchase individual stocks for short term profits. The problem is that unlike an actual day trader, investment clubs can't react quickly to changes in the prices of their stocks. At the beginning of March a club may vote to buy Pfizer, the stock may peak in mid-March and be lower than where they bought it by the time they get together again in April. And at that point, they have to vote on whether they think it'll do it again!

One club Harrington profiles attempts to deal with this problem by putting stop-loss orders on all their stock holdings: if a stock declines by 20%, they sell the stock — then frequently buy it again at their next meeting, when the price has had time to recover!

This is not a good way to invest

I believe virtually all people should save for retirement in Vanguard target retirement date funds.

But even if you have a different risk tolerance than the ones reflected in Vanguard's target retirement date funds, you probably should implement that risk tolerance through low-cost indexed mutual funds.

But even if you believe that you're preternaturally gifted at predicting the short-term movement of stocks, you should simply act on your gift by buying and selling stocks, not waiting weeks at a time and then spending time convincing your fellow investment club members that you know which direction a stock will move before your next meeting.

But creative forced savings mechanisms are pretty cool!

That brings me back to my Italian barber. He is really convinced that many members of his investment club would save nothing if they weren't saving $50 a month in monthly club contributions.

And at the same time, over a working lifetime, $600 per year invested in the broad stock market really will return more than the same $600 invested in FDIC-insured savings vehicles.

So I'm all in favor of crazy schemes to force yourself to save! Here a few I came up with that make at least as much sense as investment clubs:

  • Every time you withdraw money from an ATM, withdraw an extra $20 and set it aside for a monthly retirement savings contribution;
  • Deposit your credit card cash back rewards into a designated retirement savings account;
  • When you redeem your miles or points for an award trip, deposit the cash value of the trip into a designated retirement account — be your own mileage broker!

A final note on tax-advantaged accounts

It's no secret that I'm a strong advocate for simplifying the US income tax code. Not simplifying it and reducing rates, just simplifying it, full stop.

One reason for that is that the current configuration of tax advantaged savings vehicles (employer-based retirement and health savings accounts, traditional and Roth Individual Retirement Accounts, and the mortgage interest deduction) leads people to spend extraordinary amounts of time gaming the tax code instead of simply saving money.

In other words, once you've maximized your tax advantaged savings vehicles by contributing to a 401(k), IRA, and buying an unnecessarily expensive house, you feel like you've done all the savings necessary (perhaps adding a 529 College Savings Plan as icing on your tax-advantaged cake).

But that's ridiculous: it's perfectly legal to simply buy stocks and bonds. You can invest in a Vanguard target retirement date account in a taxable account, and it will generate the same long-term returns as the identical fund held in your tax-advantaged accounts. You just have to pay long term capital gains on the returns when you eventually sell (although you avoid the 10% early withdrawal penalty on the exact same fund if held in your IRA).

I just bricked my Bluebird account (for the next 28 days)

Today I'm going to share a very simple, very stupid mistake I made. In fact it's so simple, and so stupid, that it's unlikely to help any of my readers. But sharing is still caring, so here we go.

Background

I manage 3 full-service prepaid American Express cards: one Bluebird account (in my name), one Serve account and one Target Prepaid REDcard account (I haven't moved that one to Serve yet).

For the first year or so of managing the Serve card, the bill pay function simply didn't work. I assume this was a version of the e-mail address bug that afflicted quite a few people, but I didn't worry about it, for two reasons. First, since the bill pay function on my Bluebird account has always worked, I could simply send $2,500 per month to that account and pay my credit card bills from there. Second, I also control the external checking account linked to the Serve account, so could simply withdraw the remaining $3,500 monthly and pay my bills from that account.

When a Prepaid REDcard came under my control, I followed the same pattern, except the card wasn't linked to an external checking account, so I only manufactured $4,500 in spend per month with the card: I sent $2,500 to my Bluebird account and withdrew $2,000 per month from free ATM's, the respective limits on each kind of transaction.

Bluebird has a $100,000 limit across all Spend Money transactions

There are six activities that American Express categorizes as "Spend Money" transactions:

  • Merchant Transactions
  • Pay Bills
  • ATM Withdrawals
  • Send Money Transactions
  • Transfers back to the linked Bank Account

It should be nearly impossible to reach that $100,000 spend limit: you can only add $5,000 per calendar month in cash and $1,000 from a linked debit card, which if maxed out would only come to $72,000 per calendar year.

But I was sending myself $4,500 per month from the Serve and REDcard accounts under my control!

Bluebird customer service is surprisingly helpful

When I attempted to make a bill payment this morning, the error message simply said the transaction couldn't be completed and to call customer service. Fearing the worst, I called in immediately. Unfortunately, the frontline representative couldn't pull up my account because their system was undergoing "routine maintenance," but she did offer to transfer me to the technical team.

The representative in the technical department took just a few minutes to look up my total amount spent so far this year, which was just over $96,000, and told me I had just under $4,000 left to spend this calendar year. While I had him on the line, I made a bill payment for the exact amount he specified, and the payment went through as usual, leaving me with a stranded $900 balance until January 1, 2016.

Conclusion

I only fell into this situation because I thought I was being clever: by pooling as much money as possible in my Bluebird account, I wouldn't have to add each of my credit cards to each of the American Express prepaid accounts I controlled. That turns out to have been too clever by half.

So learn from my stupid mistake: take the time to add your payees to each account you control, and you'll never come close to hitting the $100,000 calendar year limit on Spend Money transactions.

Anatomy of an Award Trip: Summer in Europe

I've written a few times about this trip before (as recently as yesterday), but now that it's locked down, I thought I'd share one of my patented Anatomies of an Award Trip!

Getting there: Turkish Airlines to Budapest

Turkish Airlines economy award space is wide open for next summer, so I transferred 50,000 Chase Ultimate Rewards points from my Ink+ account to United Mileage Plus, where I already had 10,000 orphaned miles. The ticket is booked out of Chicago, since there's never any award space on United from our hometown to O'Hare, so we'll pay an additional $60 for two bus tickets, which I included in the total cost below.

Total cost: 60,000 Mileage Plus miles and $81.80. Total value: $2,449.20. Value per point: 3.95 cents per Mileage Plus mile.

Getting back: Air Berlin to New York City

Air Berlin award space isn't as good as Turkish Airlines award space next summer, but I didn't have too much trouble finding two economy award seats, which I booked using a combination of Avios and cash. I actually don't have our tickets home from New York City yet, but I assume I'll just throw some Delta Skymiles or US Bank Flexpoints at that problem eventually.

Total cost: 26,000 Avios and $358.18. Total value: $1,539. Value per point: 4.54 cents per Avios.

Staying there (1): 9 nights in Central and Eastern Europe

I pieced the bulk of this trip together by first booking 3 pre-devaluation pairs of nights at Club Carlson properties in Central and Eastern Europe, then filling in the gaps with post-devaluation points, plus one paid night. Here are the totals:

  • 3 nights at the Radisson Blu Beke Hotel, Budapest. Total cost: 45,000 Club Carlson Gold Points. Total value: $294.54. Value per point: 0.65 cents per Gold Point.
  • 3 nights at the Park Inn Danube, Bratislava. Total cost: 18,000 Gold Points and $2.12. Total value: $239.05. Value per point: 1.32 cents per Gold Point.
  • 2 nights at the Radisson Blu Style Hotel, Vienna. Total cost: 50,000 Gold Points. Total value: $475.53. Value per point: 0.95 cents per Gold Point.
  • 1 (paid) night at the Hilton Vienna Danube Waterfront. Total cost: $146.

Staying there (2): 6 nights in Germany

From Vienna, our plan is to spend 6 nights in Germany, split between Berlin and the home of my partner's relatives in Bavaria. I recently orchestrated a complicated trade for 2 free Hyatt credit card signup nights, so I'll likely redeem those for two nights at the Grand Hyatt Berlin, a $458.05 value.

Conclusion

Looking over the awards I booked to piece this trip together, I see that I'm consistently getting more value from my miles and points redemptions than I would by booking my flights and hotels with fixed-value points like Barclaycard Arrival+ miles and US Bank Flexpoints. That's the kind of ongoing feedback I continually use while deciding whether to collect airline and hotel loyalty currencies, versus more flexible fixed-value points.

Use a demand schedule to maximize open jaws on revenue tickets, too

The "demand schedule" is a tool I first read about at Milenomics, which has now become more or less conventional wisdom: by creating a consolidated list of all the trips you plan to take, including flights, hotels, and transportation, you're able to maximize the value (and minimize the cost) of each trip by taking advantage of stopovers, open jaws, and roundtrip pricing.

Equally importantly, when a mistake fare or generous coupon code pops up, you have an itemized list of all the reservations you need to make with it. Avoiding paralysis in that way maximizes the value you get from your travel hacking practice.

I confess I'm not terribly diligent about maintaining my demand schedule; I more or less piece together trips as award space opens up, and most of my hotel stays are paid for with Hilton HHonors or Hyatt Gold Passport points, where I almost never have trouble finding rooms available with points.

But an upcoming trip illustrates why a little planning can go a long way.

Revenue tickets can include very cheap open jaws

I have a number of pre-devaluation award nights booked at Club Carlson properties in Europe for next summer, and paid 26,000 Avios and $358.18 to book two tickets back from Berlin to New York at the end of the trip.

My initial plan was to book our outbound flights to Budapest on Turkish Airlines for 30,000 United Mileage Plus miles each, since award availability is wide open next summer. That would involve transferring 50,000 Ultimate Rewards points (with a cash value of $500) from Chase to United Airlines Mileage Plus (I have 10,000 orphaned Mileage Plus miles in my account already).

Then I realized that I still have the US Bank Flexpoints I had been saving up for this trip before I found Air Berlin award availability. I still plan to book my partner's ticket by transferring 20,000 Ultimate Rewards points to United in order to empty my Mileage Plus account, but for my own flight I decided to look into revenue tickets on the same outbound flight.

While searching for Turkish Airlines revenue tickets, I immediately noticed that a one-way outbound flight prices out at $1,010 through the Flexperks booking portal, while it's only trivially more expensive to add a return flight from most Turkish Airlines destinations in Europe back to Chicago (for example, $1,185 returning from Berlin).

Because of that fluke of pricing, whether I book a one-way outbound or a return itinerary, I'll pay 70,000 Flexpoints — an example of what I've called in the past "price compression."

In other words, I can substitute 70,000 Flexpoints for 30,000 Ultimate Rewards points and get an additional one-way flight from Europe to Chicago — but only if I can decide on the origin and date of that future flight at the time of booking! A demand schedule would help in that calculus, but I don't have any additional trips to Europe planned, aside from our summer holiday.

Is this a good deal?

There are two competing intuitions when it comes to situations like this, and I want to give each one a fair airing:

  1. since 30,000 Ultimate Rewards points are worth $300 in cash, and 70,000 Flexpoints are worth $700 in cash, a 30,000-points Ultimate Rewards redemption is $400 cheaper than a 70,000-Flexpoint redemption;
  2. since 70,000 Flexpoints are worth a maximum of $1,399 in paid airfare, and 30,000 Ultimate Rewards points are worth up to 12.4 cents each, or $3,720, when redeemed for Korean Air First Class flights, it's better to redeem the fixed-value Flexpoints wherever possible, while saving Ultimate Rewards points for those redemptions where their value is maximized.

In other words, you can think of the reservations as minimizing your cash-equivalent outlay or maximizing your option value by retaining your most potentially-valuable points as long as possible.

Finally, the paid Flexpoints redemption booked into the "H" fare class will earn 100% of the actual miles flown, or roughly 6,142 Mileage Plus miles if I credit the outbound flight to United. As long as I ever plan to transfer Ultimate Rewards points to United again, booking the paid fare will save me 6,000 Ultimate Rewards points at that time. If I book a return flight from Europe to Chicago at any time within Turkish Airlines' booking window (and end up flying it), that will add another 6,000 or so miles to my United balance.

Suddenly, we're talking about paying 70,000 Flexpoints or 42,000 Ultimate Rewards points (30,000 spent on the reservation booking and 12,000 foregone by booking non-mileage-earning award flights), and the Flexpoints redemption is looking even more persuasive.

So, what should I do?

My decision will ultimately depend on whether I can find a return flight from Europe that I'm more likely than not to actually take.

Spending $700 in Flexpoints in order to save 36,000 Ultimate Rewards points isn't as compelling as saving 42,000 would be (if I was able to fly both the outbound and return), since it moves the cash-equivalent breakeven point from just above $300 to just below $300, and one-way economy flights between the United States and Europe cost exactly 30,000 Ultimate Rewards points when transferred to United Mileage Plus (subject to award availability).

British Airways devaluation got you down? Book with Iberia instead!

The 4,500-Avios, short-haul British Airways Executive Club award has long been one of the most valuable things about the program for North Americans. On flights within the United States you pay neither fuel surcharges nor close-in booking fees, and your Avios are refundable up to 24 hours before departure (you forfeit only the taxes and fees).

Starting February 2, 2016, the same short-haul flights originating or ending in North America will cost 7,500 Avios per segment, although there's no indication the other two features will change.

The good news is that as far as I can tell Iberia hasn't announced any changes yet.

Iberia is still a weird program

The two key things to know about booking North America Iberia award flights are:

  • Awards have to be round trip. You can't even search for one-way availability; you have to use a dummy return date (or search for availability on American Airlines' or British Airways' website first);
  • Award prices are based on total trip length, adjusted by cabin.

What do I mean, "adjusted by cabin?" Hopefully the following example will illustrate the idea: a flight from Chicago (ORD) to Louisville (SDF), a 574-mile roundtrip, costs:

  • 11,000 Avios and $18.70 in Blue Class (economy);
  • 22,000 Avios and $18.70 in Blue Class one way and First on the return;
  • and 33,000 Avios and $18.70 in First in both directions.

The same itinerary connecting in Charlotte (CLT) in each direction (1,868 miles roundtrip), costs:

  • 17,000 Avios and $24.70 in Blue Class;
  • 23,109 Avios and $24.70 in First on one of the CLT-SDF legs (17.9% of the total distance) with the remainder in Blue Class;
  • 27,891 Avios and $24.70 in First on one the ORD-CLT legs (32.1% of the total distance) with the remainder in Blue Class;
  • 29,218 Avios and $24.70 in First on both of the CLT-SDF (35.9% of the total distance) legs with the remainder in Blue Class;
  • 38,782 Avios and $24.70 in First on both of the ORD-CLT (64.1% of the total distance) legs with the remainder in Blue Class;
  • 34,000 Avios and $24.70 in Blue Class one way and First on the return;
  • and 51,000 Avios and $24.70 in First in both directions.

The total number of Avios required very closely corresponds to the sum of the percentages of the total itinerary flown in each cabin multiplied by that cabin's roundtrip Avios award cost.

Observe two key things here:

  1. Under today's award chart, a roundtrip, nonstop flight between Chicago and Louisville in First is cheaper if booked with Iberia (33,000 Avios) than if booked with British Airways (36,000 Avios), and an itinerary connecting in Charlotte is also cheaper with Iberia (51,000 Avios) than with British Airways (72,000 Avios — no, I'm not kidding);
  2. After the February 2, 2016, British Airways devaluation, Blue Class nonstop flights booked with Iberia will be cheaper (11,000 Avios) than if booked with British Airways (15,000 Avios).

Takeaways

Here are a few things to take away from this post:

  • You can only use Iberia to book roundtrip partner itineraries;
  • Do not use Iberia to search for partner award availability;
  • Once you find North American award availability with American Airlines or British Airways, check their prices against Iberia's;
  • Iberia's online booking system is very frustrating but very flexible — it's easy to book short legs in Blue Class and longer legs in First for potentially big savings, because of the "cabin adjustment" mentioned above.

Conclusion

Using Iberia Avios instead of British Airways Avios for short-haul North American flights isn't a silver bullet to solve all of your award booking problems. But it is another tool you can use to let your miles take your further, faster.

Don't retire to hotels, live in them!

I've written a few speculative posts in the past based on the conceit that manufactured spend makes staying in hotels full time a cheap way to save on rent in retirement.

I recently joked on Twitter that it's cheaper to stay at the Hilton in San Francisco than it is to rent an apartment there, which got me to thinking: are there really places where the rent is so high that living in hotels could make practical sense?

Methodology

To compare the cost of renting versus monthlong hotel stays, I used the figures in this recent CBS News article about median apartment prices in the 10 most expensive cities in the United States. These are median, not average, prices, so 50% of rental units are less expensive and 50% are more expensive.

I don't have any reason to trust these numbers, compiled by ApartmentList.com, but at least they give us some concrete figures to work with.

I then looked at the imputed redemption value of a 30-day stay with four programs:

  • Hilton HHonors (manufactured with an American Express Surpass card at gas stations or grocery stores at an imputed redemption value of 0.35 cents each and redeemed in blocks of five nights, with the fifth night free);
  • IHG Rewards (purchased during a fake reservation at 0.7 cents each);
  • Hyatt Gold Passport (1 cent per point transferred from Chase Ultimate Rewards);
  • Choice Privileges (manufactured with the Chase Choice Privileges Visa at an imputed redemption value of 1.0525 cents each).

In the case of Hilton and Choice I compared their earning rate to the 2.105 cents per dollar earned everywhere on a Barclaycard Arrival+ MasterCard.

Wherever possible, I observed the following rules:

  1. I used the actual municipality given by CBS News/ApartmentList.com, so in the case of Oakland I excluded properties in San Francisco, and vice versa (the exceptions were Los Angeles, which doesn't have a Hyatt property downtown — I used the Andaz West Hollywood instead, and Miami, where I included Miami Beach properties);
  2. I used the cheapest property located within the central area of each city, with the exception of Washington DC, where I used the Holiday Inn Washington-Georgetown.
  3. Where seasonal adjustments were small, I used the smaller figure as long as it was realistic. In one case where the seasonal increase was over 100% (Bluegreen Vacations Solara Surfside, the Choice property I used in Miami) I gave both the high and low season figures;
  4. Large seasonal variations are the rule with Hilton HHonors, so in all cases I gave both the low and high season figures.

Finally there's an additional wrinkle worth noting: since hotels offer both award stays and paid stays for the same nights, you should be able to reduce your actual expenses below the imputed redemption values I give by paying cash for those nights where the cash rate is lower than the imputed redemption value of an award night.

Results

Here are my results, in all their Excel spreadsheet glory:

For each city, I've highlighted the chain with the lowest and second-lowest imputed redemption values. That leads to a few observations:

  • In four of the ten cases, the Hilton properties have the lowest imputed redemption values whether or not the property is charging low-season or high-season prices;
  • In four of the remaining cases, the Hilton property is cheapest during low season and the Hyatt property is lowest during the Hilton property's high season. In these cases the logical thing to do would be to move from Hilton to Hyatt once high season pricing went into effect at Hilton;
  • The IHG Rewards Club property never has the lowest or second-lowest imputed redemption value.

These results so strongly confirm my biases towards Hilton and Hyatt that I had to double-check my math to make sure I hadn't tampered with the scales.

Hilton's dominance seems to be a mechanical product of two facts: earning 6 HHonors points per dollar with the Surpass card, and taking advantage of the fifth night free on award stays. While Hyatt typically charges fewer points for award reservations than Hilton, they have to charge 72% less to get an edge on Hilton. Since Hyatt doesn't charge more for rooms during high season as Hilton does, that's where their edge tends to emerge.

Conclusions

From one point of view, my original question was answered conclusively: in none of the top ten most expensive rental markets are monthslong award stays cheaper than renting the median apartment.

This conclusion should be taken with a healthy dose of salt, however:

  • as noted under Methodology above, you can save money over award stays by swapping in cheap paid nights over weekends and during low season. Doing so will also trigger points earning, which reduces the total amount of manufactured spend necessary each month;
  • as a top-level elite, your stay at many properties will include a continental or hot breakfast, and may include dinner as well, depending on the food spread available in the property's lounge;
  • this research compared the median rental property in a city to downtown chain hotel properties. Depending on the city, the median rental property may be in much worse condition, in a much worse neighborhood, much farther from downtown. In other words, if you're an upper middle class travel hacker working in San Jose, you're probably not living in the median rental property in the city, and you're probably paying much more in rent than the figures I cited.

Finally, while I intentionally framed it that way, living in hotels isn't an all-or-nothing proposition. For example, you may find that moving into a hotel for a month while you're between apartments, or in the process of moving to a new city, offers savings compared to other short-term housing options, or convenience compared to staying with friends or renting a room on AirBNB.