Bnewb. I think this can't be stressed enough. There have been scores and scores of people that I have either personally known or that I have met through forums like here who thought they were prepared to move to Jamaica permanently and have since left disillusioned by the experience. It is not like moving from say Omaha Ne. to NYC although a shock to the senses that would be. Everyday life in Jamaica can wear you down. Things that are common place and easy where you live can be laborious and frustrating in Jamaica.
Although I now live in rural Jamaica, if I didn't go back and forth once or twice a year I would pull out the little bit of hair I still have. We have a saying in my hometown that "there are 25 hours in a day and 8 days in a week" to describe how slow time seems to go there and planning things around "likkle more" and "soon come" can be nearly impossible. I have stayed for multiple months in five different locations (Kingston, Port Maria, Treasure Beach, Accompong Town and Negril) and each presented me with different challenges to overcome.
My advice to someone wanting to move to Jamaica might include:
1) Be sure you have more than enough steady income (Being retired helps because finding a job and getting a Work Permit is very hard) Everything will cost more than you plan for.
2) Use some money to go to Jamaica at least 3 times in one year. (Tourist Season, middle of Summer and Fall) Each season has different challenges.
3) Stay for at least a month each time (being the "fresh face" and being a "veteran traveler" can be quite different)
4) Explore different areas. (Your dream might be the beach in Negril but your wallet might not be fat enough to keep you there)
5) Choose your friends VERY carefully. (Man to man is so unjust, children: Ya don't know who to trust.Your worst enemy could be your best friend,And your best friend your worse enemy.Some will eat and drink with you,Then behind them su-su 'pon you.Only your friend know your secrets,So only he could reveal it. - Bob Marley was SO right about that).
6) Keep your financial situation to yourself (No need for anyone to know how much you have, how much you can get or where your money comes from)
Consider trying to split between your home now and staying in Jamaica as you will have to leave at least once a year for one day anyways to satisfy immigration rules. Six months in each place will let you know in a couple of years just where you really want to live. Jamaica is nice but noh easy.
Peace and Guidance