I do a lot more bean-counting on the earn side than the burn side, with the latter a bit more emotionally driven. Award flights are often a chance to get to someplace otherwise overpriced on paid tickets, but that place must have some appeal. Last year I used KE miles dating all the way back to 1992 for an ICN-ULN trip to go see Naadam in Mongolia as part of a wider Asia trip. Also went around all the CO Micronesia places except Chuuk on awards, as well as a chunk of the South Pacific on NZ with UA miles (acquired during the great Amtrak transfer of the early oughts...I still get occasional mail from Amtrak thanks to that).

Alaska in September at 25K also is a bit of a fixture, and with Spirit you can do very well on free trips IF you have the credit card and IF you can travel in spring and fall and do it very lightly.

Sometimes the toughest calls are positioning flights. I spent 35K DL miles on a MEX RT to position to a LA deal for IPC and an SCL stopover at just over $500. Was upgraded in both directions to MEX.