They sure all do have their benefits and drawbacks, you need to figure out what your priorities are and work around them.
An important issue you haven't included is visa/land ownership for foreigners. That might be the best place to start, since it rules out a few countries almost off the bat. Another is ease/cost of travel if you're going to be coming back and forth to the US. It mounts up real quick.
As with all things, there are exceptions to everything, so you might need to visit places before ruling out an entire country because of crime, for example.
I've been a US expat in south america for 12 years, and I work in consular outreach. While I own a small urban homestead in Brazil (where, as mentioned above, it FROSTS! who knew), and I love it here, I would not recommend it to anyone. I'm here because of family, if you don't have social support and the language there are just too many hurdles to overcome, and with new political regime it's about to get much more complicated, unless you're the kind of person who throws money at problems.
In general, people talk about Costa Rica as having infrastructure that is most accepted by Americans. Nice people, calm country. I'm also hearing a lot about Panama and Ecuador as
retirement places, but I am not sure about land ownership in any of these countries, and that will be important. But I know people moving to off-beaten-track Mexico who seem to be very happy.
Edited to add: it can be really hard to get things in these countries. When you have bugs eating your tomatoes, and every site suggests
diatomaceous earth, and that product simply doesn't exist where you live, it gets frustrating. Getting Amazon shipping is not a possibility in some places (Brazil just put a law in place that it costs $15 to receive any mail from abroad. Even a postcard. Shipments from abroad, you pay a tax that is what the revenue service believes to be appropriate for your shipment, including shipping costs. I bought a pair of contacts for USD 5 and got free shipping. Cost me $300 to bail them out.). It seems like a silly detail, but when you want a broadfork, or seeds, or your rototiller busts a gasket, it can be problematic. When you move definitively you can often get exempted from taxes if you have residency, but that is a one-shot deal so you need to plan well.