How looking at reservations in isolation makes me overpay for travel

There is a mistake I consistently make in my travel hacking practice: I compare every travel purchase I make to its lowest-cost alternative in isolation. For example, take an airport like LAX with nearby properties in multiple hotel chains. Glancing at a site like Awardmapper, you can compare these locations:

• Hilton Los Angeles Airport (32,000 — 40,000 points);
• Hyatt Regency Los Angeles International Airport (12,000 points);
• a couple of Wyndham properties (15,000 points);
• Four Points by Sheraton Los Angeles International Airport (10,000 points);
• and Holiday Inn Los Angeles - LAX Airport (30,000 points).

You can do a quick calculation based on your own travel hacking practice, but using my values I'd come up with a cost of $160, $120, $150, $200, and $210, respectively, as the imputed redemption value for each of those properties. That's not the out-of-pocket cost of acquiring the points, but rather the foregone rewards on a 3% cash back card in the case of Hilton, a 2% cash back card in the case of Wyndham and Sheraton, a 1 cent cash back redemption of Ultimate Rewards points in the case of Hyatt, or a 0.7 cent-per-point purchase of IHG Rewards points in the case of the Holiday Inn (although you can almost always do a bit better than that).

So far, so good. If the cost of a suitable hotel were less than $120, I'd book with cash, and if more, I'd book with points, in this case probably 12,000 Ultimate Rewards points transferred to World of Hyatt.

This makes me too hostile to rewards gimmicks

I've written plenty of times about how much I dislike the annual companion ticket that comes with my Delta Platinum Business American Express card. The problem with it is simple: you have to pay for the primary passenger's ticket (and the taxes and fees for the companion) with an American Express card, and that means paying cash. If you'd otherwise buy your ticket with US Bank Flexpoints, for instance, then a sub-50% discount (with only one ticket earning flight credit) just isn't that impressive compared to the roughly 58% discount I'd get on a pair of Flexpoint redemptions, both of which would be eligible for earning and upgrades. Adding in the $195 annual fee makes the companion ticket an even worse value.

Likewise I have no use for annual free night certificates at chains I wouldn't otherwise stay at, since the additional cost of staying more than one night would eat up any potential savings on the first night.

This is fine, as far as it goes, but is also the source of the mistake I'm talking about: I also have to pay with cash if I don't have enough points to redeem for my airline tickets, or hotel rooms, or car rentals, or whatever. Now, I can put the charge on my Arrival Plus card and get trip delay insurance, and maybe redeem $100 in rewards as a statement credit against the purchase sometime in the future, but that's no substitute for an up-front 58% discount.

Travel hacking ideally reduces your total out of pocket costs

That brings me to the point of this post, and what I'm sure is a better way to ultimately implement a travel hacking strategy than mine: getting the biggest discounts on the expenses that are hardest to hack, and accepting smaller discounts where necessary in order to reduce your overall travel costs.

Some stylized facts demonstrate this clearly:

• Two $400 roundtrip tickets booked using a Delta Platinum companion certificate would cost $405.60 (depending on connections), plus a $195 annual fee, for a total of $600.60, a 25% discount.
• The same two tickets would cost 53,333 Flexpoints, representing $26,667 in grocery store spend, costing roughly $337 in activation and liquidation fees, a 58% discount.

If your only travel expense during the year is buying two $400 Delta tickets, then you're obviously better off redeeming Flexpoints and realizing a 58% discount than using a companion ticket and saving just 25%. And indeed, this is my main argument against companion tickets that require you to pay cash.

The problem with this logic is that the 58% Flexperks travel discount can be applied to a whole range of travel expenses, now even including travel expenses made directly with the vendor under certain circumstances.

If you had unlimited access to manufactured spend, you would always have enough points to redeem and pay the lowest possible amount out of pocket. Whenever Hilton, or Hyatt, or IHG offered the largest discount, you'd book with those points, and book flights with miles, Flexpoints, Ultimate Rewards points, or whatever other currency offered the lowest out-of-pocket cost.

But if you have finite access to signup bonuses, manufactured spend, airline credit, etc., then misallocating those currencies can mean paying cash and realizing no discount at all on some expenses. To return to the example above, if in addition to your $800 in airfare you also need an $800 hotel room, then you'd be better off taking the 25% discount on your flights and applying the 58% discount to your hotel, instead of taking 58% off your flights and 0% off your hotel: $937 is less than $1,137.

Framed in this way the solution is obvious because both expenses are connected to the same trip. Over an entire year, that won't be the case: sometimes you'll fly American instead of Delta, you'll fly internationally instead of domestically, you'll have sub-$500 hotel stays that won't qualify for Real-Time Rewards redemptions, etc.

It's that inter-temporal coordination problem that causes my sloppy thinking and leads me to pay more than I would if I optimized my redemptions across longer planning periods.

Conclusion

I don't think there's any shame in being wrong, but you do tend to run into problems when you refuse to admit you're wrong, so I fully admit this is something I'm wrong about: I try to redeem miles and points as aggressively as possible, even when it leaves me holding the bag and paying cash for tickets or hotel rooms I could have gotten a better deal on if I sorted my redemptions by value ahead of time.

I'm so resistant to paying cash that I deliberately book my Delta companion ticket on the cheapest flights possible, even if that means redeeming far more Flexpoints or Ultimate Rewards points on more expensive flights in the future.

But you don't have to be as dumb as me! By planning ahead and creating even a crude demand schedule, you're much more likely to lower your out of pocket costs by using the right rewards tool for the right job.