Thanks, this is just the kind of help thinking through options that I was looking for. I like your ideas about the SJO overnight on the return, and I don't mind taking Amtrak to and/or from NYC.
But let's assume that we want to travel up front and don't mind blowing the entire 280k in one trip. So that means anything for 70k per business class award. I'm very interested in possible routings to Curacao or Margarita, less so Colombia due to the civil war there. I would also be interested in Belize or Roatan, but they are unreachable from IAD with the SAL overnight. Are there even any hotels near the airport in SAL?
I know very little about destinations in South America other than Quito and Cuzco. I'm looking for somewhere I can take kids aged 10 and 13 without too many hassles. Peru, including Cuzco and maybe one other spot might work out well if I can make it down there in a day. However, I believe an overnight in LIM would be required to catch the early morning flights Cuzco.
Also, didn't there used to be a limit on flight segments in LP awards (maybe 3 in each direction)?