A near miss....
I was trying to book a trip TPA-MSP-PIR a couple months ago using AS miles and got so focused on using the miles that I lost sight of the forest. I paid for 2 tickets at something like $450. For some reason having to do with the NW/DL merger, I was unable to find availability from TPA-MSP so was going to buy that portion for $250-ish then use 25k miles+various fees for MSP-PIR. After I booked it, I came to my senses but by that time it was too late. Fortunately, schedule changes resulted in serious misconnects and everyone involved let me cx both the TPA-MSP and the MSP-PIR portions for full refunds and I could just buy 2 additional tickets like I should have originally.