HOUSING: Are you planning to rent, build or purchase a previously built home?
POSSESSIONS: Are you going to ship your previously owned possessions or replace them after you move back to Jamaica?
TRANSPORTATION: Do you need a vehicle (ship one or purchase one there) or can you use public or private transportation?
SCHOOLING FOR SELF OR CHILDREN: What options will be available where you are planning to live?
JOB OPPORTUNITIES: Find a job? Work for yourself? Investing your capital?
BANKING: Does your current bank have an office in Jamaica? Can you find a financial institution that can provide you with all the services you require?

Plan on taking a trip to Jamaica for a month or more before making that final move. Get to know your country again. You should be able to have definite answers to the above questions before you make that move.

Source Jamaican Embassy