It's possible to live very nicely in Jamaica. I was in Negril and you can rent whole houses there near the beach for only $250 US. The internet connection is decent since there are tourists there. They even have a few internet cafes. I would only try living in Montego Bay or Negril to get anywhere near US standards.
There's also a white boy who lives down there and hangs out with the ganja farmers and sells ganja videos. I met him while i was down there. His website is at
http://www.rastajohn.com
The only thing I hated in jamaica was the roads. They drive way too fast around winding hilly roads and I don't think my nerves could deal with that. Plus they drive on the left side of the roads and their steering wheels are on the right. I would fear a car crash especially since their hospitals aren't near the quality of the US. Plus if you're white, you're going to get treated differently everywhere that you go and you'll only be really accepted by other American Ex-patriates. If you're black, you stil will not be fully recognized but you'll be a whole lot closer to the real jamaica than the white man ever will.
Other than that, I could buy pounds of Ganja for a few dollars, there's also plenty of cocaine if you like that. I had plenty of fine jamaican big booty hoes around that will do almost anything for under $100 US. And if I wasn't so lazy, I could have eaten very cheaply if I was willing to buy and cook my own food. Plus you could bring in a few girls from other countries and pimp them out to the american tourists for extra cash ;)
But even if I was in a paradise, I'd still miss america. Even though they have Kentucky Fried Chickens and Burger Kings, I'd still be homesick. There's no place like america. I'd get tired of all of those fuckin jamaicans up in my face day after day or any other group of foreigners for that matter. But all in all, if you want to move out of the country and don't have any kids yet, Jamaica would be a good option.
Bottom line is if you decide to move out of the country, you not only need money to live when you're there, you need extra money to fly you and your family back and forth if there is ever a family emergency, you need extra health insurance, you need a car, and little shit that costs a fortune overseas like toilet paper and razor blades. Plus you have to train your stomach to deal with all of the new bacteria of the country.
A good alternative would be to move to the virgin islands or puerto rico and just keep a po box and bank account in the bahamas or belize.
I've been thinking about retiring to the caribbean and not working since I was a young child so believe me, I've put a LOT of thought and have done a decent amount of travel to explore my opportunities.