Central America ? ...... I would move to Costa Rica in a heartbeat. There are a huge number of Americans living there now. Beautiful country, stable, great coffee, a great health care system that thousands of Americans use, at about 30 cents on the dollar compared to the US.
The Caribbean is a bit dicier. A lot of the countries are divided between the haves and have-nots. A lot of crime in many places. Just very expensive in some of the better areas. I could go into detail on many of these countries but if I was moving to the Caribbean my first choice without doubt is part of the US, Puerto Rico. My wife and I have already thought about retiring there in the future.
If I ventured further out beyond my comfort zone, the Dutch territories, Aruba, Bonaire and Curacao would be my next choice. Curacao would be my first choice. They are far enough south that you don't have hurricanes but then you have to get used to the fact that you get very little rain ... not really tropical-looking like South Florida ... kind of barren in some ways.
The Bahamas is also an option being so close to Miami (Bimini is only 45 miles from the US coast) if you don't mind driving on the "wrong" side of the road (the left side). If you have a boat, it's about an hour to an hour and a half ride depending on what type of boat you have.
Overall, I really like Puerto Rico.
Rub a Dub