I had residency and a work permit from 1969 - 1984. Didn't leave the Island for 3 years once. After 1975 I was in business for myself but still had the work permit.
After 1975 I would "go and come" every few months.
Now that we're retired we just arrive on a visitor's visa. And we'll stay that way.
We love our home in St. Augustine and like to visit family and cruise (I need to be on a ship every so often)
I can't imagine being in Jamaica more than 3 mos at a time.
That's just our story. Each immigrant/ex-pat/resident/regular visitor has their own individual situation.
My advise? Test the waters before you jump in up to your neck
No amount of 10 day visits can really prepare you for living there. Also, having your own house and property is a different experience than renting.
Just my opinion
Cap