So some folks have mentioned that PR has not been the only place to catch their eye. Same for me. Figured I'd start a thread on that topic. Where else have you considered?
Like many, I've considered the DR. Similar in climate and culture to PR, and the cost of living is comparable as well. PR gets the nod because of its legal relationship to the U.S. If I were dependent on the local economy for my income however, that might change. The DR is doing fairly well, and there is reason to think that the local economy will continue to post solid growth.
I've also looked at Colombia. This is a Latin country moving in the right direction. Agreements with FARC and ELN make the country much more stable. Close relations with the U.S. Drug problems are still an issue, but the state is much more effective than it was even ten years ago. Property values and cost of living are low. Costa Rica and Belize have been popular for too long -- in my case those ships have sailed. But I think Colombia has the potential to be the next big thing in the Caribbean.
PR has the advantages of climate and culture. The disadvantages such as economic contraction and a deteriorating infrastructure are manageable in my case, since I plan on relying on investment income and will generate my own power and collect my own water. Originally I planned on solar and cisterns to shield us from rate hikes as the government tries to raise revenue. But considering the interruptions in utilities, which will likely only get worse as the budget shrinks, self-reliance strikes me as the only reasonable course.