Hey!
Well you can def buy a practice in the caribbean sin the US$ goes a long way. If you are looking for english only, i wish you luck. PR has both going on, but in reality is mostly Spanish and the crime is beyond words. Cuba, out of the question since is a Spanish speaking environment in terms of pt and laws. Dominican Republic has a few dental schools that teach in english, and pt that are english speaking but that population is (1%). To live there is good, since your us$ can go long, the weather is great. If its not Jamaica, Dominica, Barbados etc you will find english speaking but it won't be as "natural" as here. Also the pt pool, the ones that will pay you your jobs worth, will be pt that are comfortable(2% of population) or well-off or other tourist. And for that you have to think of your location. If you're trying to start from scratch and have a good income, is a bit hard to do, my friend but not impossible. You have to remember that these countries or island have their own grown dentist and their prices at times are so low, is really hard to compete with them. And their work is superb! So do your research first.
FYI: i am american and i became a DDS in a caribbean dental school. I worked/volunteer in other countries (haiti, puerto rico, dominican republic, mexico) as well, as part of building my resume. (so that's why i have an idea lol)
Good luck in all your endeavours!