Hi Sandy Toes (Kim). Now, this is just my opinion so just understand that I have been to Jamaica at least twice as often over twice the length of time and have been staying 3-6 months at a time although all over the island and only a few times in Negril on the West End. I am currently staying in rural Westmoreland...and I stress..RURAL.
I started out wanting to live full time in Jamaica and, in the early '80s was spending the majority of the year in locations like Treasure Beach, St. Mary, Kingston and St. Elizabeth (Accompong Town). As much as I loved and still love Jamaica, I find it to be frustrating at times and somewhere just over the halfway point of my stay, looking forward to returning to the US. Living in Jamaica or Negril (which is not hardly like living in Jamaica) for 3 - 6 months suits me fine. I would not IMHO plan on a full time move until you have a couple of years of 3 - 6 months under your belt. My hats off to people like Rob and Lisa who made the move and enjoy it most of the time I would guess.
Being a frequent tourist is not the same as living in Jamaica or Negril.
I concur with Bnewb that going to Negril and looking for a place with money in hand affords the best options.
I wish you the best of luck in whatever you finally decide.