I've had 2 friends do similar, one to work remote from the US Virgin Islands and one to do remote from a beach town in Brazil. One was successful, one was not.

I've had 2 friends do similar, one to work remote from the US Virgin Islands and one to do remote from a beach town in Brazil. One was successful, one was not. The issue seemed to be that in many towns the ex-pat community was small and was made worse in areas where most of the house are absentee owners. A small town can be made smaller if the houses are vacant or swapping out renters every week. It also makes community stuff think like softball leagues (or whatever hobby you have) difficult. Anyway, if you can do this, make sure you can find a community wherever you go!