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The thought crossed my mind as well as "what if I did something crazy and sold everything and moved as far away as I could without the logistical challenges of changing countries" and who knows, maybe I'll seriously consider doing that once my grandparents pass away. There's bound to be someone looking to hire an IT person in Puerto Rico for a year or two. On the other hand I'm sure there's a lot more heat and sun to deal with which I'm not a huge fan of...so Alaska maybe?
I'd also recommend being close, if not fully, fluent in Spanish.
If not fluent, yes you'll have a hard time. I've been there and outside of the tourist areas, people either can't or won't speak English.
I do recommend the USVI if the language barrier is a problem.