Funny, but my "why Jamaica" ties in perfectly with this recent discussion - my friends. Over the years I've made many - expats, Jamaicans, "long termers" - those were the folks that inspired and encouraged me to make my long term stays....so now when I go its to see "family" and be with my community.
Everyone's community is different and everyone is drawn to different people for a variety of reasons. The expat community in Negril is quite small. I don't necessarily like or hang out with all of them. I don't relate or have anything in common with all of them. But my community is tight and like-minded on many things. We share more than just a love for a location.
In recent years I've got a bug in my butt to explore more of the island. Never really used to...but we venture out of town quite regularly now. My trip to the North Coast this winter was a huge inspiration to do more, more and more of that type of thing. My home base will always be Negril though. That's my "other" soft spot.