Hi and Good Day
For anyone wishing to retire in Jamaica you may be more comfortable if you have your own home that is mortgage free. You will need to pay an annual Land Tax fee for any privately owned land.
If you choose to live within a gated community there will be a monthly 'maintenance fee' that includes the upkeep of the community (not withstanding the actual properties) areas, roadways, facilities, street lighting, garbage collection, sewage waste collection and may include cutting the lawn once a month.
Where ever you live you will have utility bills to pay. If you are 'off grid' this may not include some utilities. You can choose to build a 'green' property, or add eco-friendly features that can lower on-going living costs.
Food, household items, good quality clothing / accessories / shoes, electrical items, bedding and soft furnishings, furniture, beds and mattresses and nearly everything that is imported is expensive in Jamaica. Ship as many items as possible and stock up on items so that you don't have unnecessary expenses. Think about growing a little this and that, have fruiting trees and nurture your spirit with fresh home grown fruits and veg. Socialising in Jamaica can be expensive depending on what you like to do.
The wages in Jamaica are low, even for some of the hardest workers, such as medical workers. However, there is a market for your skills in the private sector where you could assist by working with people performing home visits. Look closer to home to make your contacts, there are many people living overseas with elderly relatives living in Jamaica who could do with this type of service. Make them know you are open for business in Jamaica in the coming months.
I wish you luck.