Your suggestion is probably going to be the reality. We are already planning on spending the summer in Colorado Springs, as that is where we'd move if we stay stateside.
Hmmm, I'm curious -- what is the big attraction in Colorado Springs? Yes, snow and 60-degree days in the winter are nice, but...
My wife grew up in Colorado Springs, school in Fort Collins, worked for the governor in Denver, etc. Came out to DC working for a CO congressman (David Skaggs), which is how we met. The family lived about two blocks from the Broadmoor, and when her mom finally died, none of the five kids wanted the (very nice) house. A shame, really. Especially for us, since we were married in the back yard..
Ourselves, we'd be much more likely to head up toward Boulder or Black Hawk.
There are a lot of realities in Costa Rica, as well. We have two tennis friends, German and Dutch, who ran their Dutch flower exporting business for many years from the Puntarenas area, but when they retired, they headed up here to the Sarasota area. The only thing they still go down there for is serious dental work -- oddly enough, it's a bargain down there.
And another couple, who retired (he) from being food and restaurant critic for an L.A. newspaper, and (she) from a career in nursing and wine importation (don't laugh!) to Tamarindo, and enjoyed it for about two years -- until they were victims of a home invasion, tied to chairs, pistol-whipped, etc.
As they say around here, get samples -- with extended stays in the places you're considering.