Introduction
Conventional wisdom is often good at the macro level, and frankly terrible at the micro level. Need an example before we dive in? Let’s start with a doozy: “If a deal seems too good to be true, it probably is.” Street smart, for sure. But also, someone following that advice would have missed out on six to seven figures in Pepper gift card resale profit, $1,000 for running a $1 charge, buying unlimited AA miles for less than a half cent each, or hundreds of other churning greatest hits.
Today’s Contestant
Let’s go over another of my favorites: “buying miles doesn’t make sense except to top off an account”. There are definitely examples where that’s true, but especially on the high end of hotels and flights, that’s often wrong. I guess we’ll illustrate with a concrete example because reasons:
Let’s say you want to unlock one of the 2010-2019 achievements in churning: Five nights in a Sunrise Water villa at the Conrad Maldives, on let’s say July 1 – July 6, 2027. As of this writing, that’ll cost either:
- $5,609.29 with the Honors discount
- 640,000 points (160,000 nightly*4, the fifth night is free with Hilton)
That looks like a ton of points! But, Hilton will often sell you points at 0.5 cents each above board, so the $3,200 you’d pay out of pocket for those points is more than $2,400 savings over the cash price, and with better cancelation terms. Neat eh? You don’t need to buy points to top off an award redemption, you can buy points as a proxy award redemption.
It gets better though, if you’re buying points from a (churning) friend, rates are quite a bit better than the rates programs will sell them to you at, and you may get that same 640,000 Hilton points for $2,600 or less. Of course, there’s some sketch involved.
Tripping You Up
It’s not all roses though, sometimes there are road-blocks and speed-bumps. For example:
- Some programs limit how many points you can buy
- Gray market transactions are gray, unless you’re in the UK where they’re grey
- Points aren’t always on sale
- Award redemptions don’t earn points like cash bookings, so you’re forgoing a modest point-earning rebate
Good luck friends!

Next time: Debunking conventional “buy more and save wisdom”.