The first time I had a private chat with my current wife, I told her "I'm going to retire in Jamaica." Now that I'm retired, we stay in Negril for an extended time in the winter, but I really like where I live in the mild weather seasons. We especially like our home and bed!
We have friends who stay even longer than we do. One couple stays almost 90 days way out on the west end in a rental cabin and another couple own a home they had built up in the hills near Green Island, stay long enough that they have to renew their visas. I find neither all that attractive. After overhearing a conversation at Tree House about land for sale, the home owners spent years acquiring the property, years more introducing themselves to the local builders, building a road that is impassable and finally their home. It's a beautiful home with a view of the 7 mile beach, but too remote for my taste.
In any event, you can rent a nice place in Negril for less than a mortgage payment in foreign, and bnewb notes stay up to 180 days/year. Why bother with permanent residence and owning a home? Respect --Marblehead