USVI and maybe PR are good deals for American citizens. One must have a spatially independent income stream, or industrious to make it there, but quite a few mainland Americans have created their American Dream. These are not the drunks and dreamers, but the doers.
Why not buy up some beach front property in a relatively under developed part of DR and set it up as short term (one to three month) rental homes. Encourage people to live out these dreams. DR is perfect -- cheap to get to from the USA, not too scary, not extremely expensive. I believe that all the planning and decision making inherent to travel discourages people -- especially now with the internet and the limitless amount of choices available. I think if you had a few nice places all set up in the DR to live in you could keep them rented out all year round and very well funded in your travels.
People do not like indecision, follow Pato's advice and set up some short term rental homes, of course if you plan to keep traveling, you will need to hire a part time ex pat or local manager to service clients when you are gone, wonderful for wanabee ex pats who wish to stay 1 to 3 months in DR to look around for more permanent rentals, that is why Central America is getting popular, lots of foreigners are moving into El Salvador and investing now as persons learn that they feel safer here than in Guatemala and Honduras, near to US and gringo friendly, only those who use no common sense and get intoxicated in bars to the point of being vulnerable get into problems, same a s at home.
It is not humid here, and strangely in Sosua there is not a mosquito problem. We have a door that is open 24/7 and no mosquitos come in. Now, we are on the ocean, and there is a good breeze most of the time. I think during August it become too hot here.
I owned up to 30 homes, and I have purchase 60 plus, there is not enough money on the planet to get me to own rental homes.
I do not live here, and I am not going to live here more than 2-3 months at a time.
No Mosquitos? Amazing! The world is full of surprises while we were traveling in Vietnam, also a tropical country like the Philippines with a population explosion we didn't see any roaches, rats or mice even in the central areas of the two largest cities Hanoi and Saigon ( finally two days before my wife flew back to MNL we "splurged" on a U$20 hotel room with expensive furniture and fixtures and saw our first "flying roach" ).
One of our old friends, "Chico" is from DR but based in Miami for many years. When I think of the Caribbean islands I always think of them being overpriced being too close to the States and massive American group tourism. Sometime next year I plan to pass through so glad to know that budget travelers can still afford to stay there in beautiful places without being forced to pay the group tourist influenced higher room rates.