For example, in Yehudas post he talks about staying in a hotel room that would normally cost him $1,000. I don't know what value he got and what points he was using but for arguments sake let's say the points were worth 1.4 on the open market and he got 4.0 by spending it on the hotel. So he spent 25,000 points which on the open market is worth $350. I wouldn't pay $350 for a hotel room - would rather go to a nice clean hilton for $200 and pocket the extra $150 per night.
While that may be true if he's shelling $350 out of pocket, it isn't true if he has already earned the points and instead of selling them for $350 he can redeem them for $1,000. I don't remember what it's called, but once you have the points you're cognitively biased to choose differently than if you had cash.
Also, AJK will probably spend 15,000 hours on vacation or online planning trips. As a lawyer, 15,000 hours at $200 an hour would've net him $3,000,000. Invest that wisely and you could retire at 65 with $100,000,000. With this amazing logic, DDF cost AJK's shul a 10 million dollar donation from his maaser. Dan is at fault here so Dan owes AJK's shul $10,000,000.
I don't think AJK will spend anywhere near 15,000 hours planning trips, that's like 8 hours a day, every single day, for nearly 6 years...
But if he did, then he didn't just lose out on $3mm in billable time, he lost out on the value of experience gained billing 15,000 hours, arguably worth much more than $3mm...
