Here's my story Romae - been traveling to Jamaica since '83...been living here "part time", 2-3 months a year (NOT retired) for the past 10 (West End Negril). I live in a neighborhood, in a private yard and am part of a community. Its a very comfortable and easy sitch. I do understand most patois and don't often encounter any hostility from anyone whether I'm in my 'hood or on the beach or walking the road. I mind my own business, I keep to myself, my community and friends I have here for the past 20 or so years. I used to think I wanted to buy land here - I'm so over that. I used to think I wanted to "retire" here - not possible...on many levels - especially in Negril - too expensive and NO healthcare. At least my crappy insurance in the states allows me to get SOME kind of decent healthcare.
One learns the runnings by experiencing the runnings. That's all I really have to say on this topic. I love my island home for as long as I have it - but I also love my California home. Life is too short to live somewhere you hate and to do or work at something you hate. I'm fortunate to love both what I do and where I live be it in the winter or fall/spring/summer.