Whether you are local or foreign to any English-speaking island or country in the Caribbean, regardless of your dreams or yens, I suggest you forget about aviation as a career.
Being a pilot is no longer a glorified or glamorous job - and maybe it never was. You bust your chops for very little money, possibly sometimes working all night, and the bean-counters around the world have made sure that what pilots lost they gained (airline CEOs and CFOs make millions now while their companies struggle) and they are still working on breaking pilots down further.
McIdiot O'Deary in Ireland's RyanAir wants to be able to fly all passenger jets with one pilot - and cram in more of his paying self-loading cargo (pasxsengers) by making them stand up for the entire flight!!!
Think about it - and I'm not joking.
Caribbean pilot salaries have historically been about half of the "developed" world, and BWIA's pilots used to make less than LIAT's. When BWIA became CAL, all the employees, including pilots, were fired and hired back without unions at even lower salaries.
TTALPA only just got recognised again after 5 years and has NO power.
So CAL pilots will make even less than BWIA pilots used to... take my stupid advice... if your family has the money, look for a different profession to get trained in - accountant, lawyer, doctor, dentist, whatever. Do something ELSE that you like to do, and you and your wife/children will have a far happier - and more prosperous - future. You may even be able to afford to buy your own home...
Forget this pilot thing, there are currently over a hundred experienced Caribbean pilots forced to find a different way to earn a living. If and when vacancies occur, the rich Daddies of some of them have already pulled the necessary strings to make sure their little darlings are high up in the line.
When you get rich at some other profession you can rent an airplane and get a pilot licence, then buy your own airplane and fly yourself around where YOU want to go. Or travel First Class on CAL, beg a visit to the cockpit and see how the other rich peoples children get their kicks - while they rent their domiciles because they can't afford to buy.
Sorry to sound so sour, but reality is reality, and today's reality in the Caribbean is pretty damned sour.
The hard reality is that you would be far better off finding a profession where you can make a good living without being kicked around for just a few bucks by rich people and politicians - most of whom seriously do not have a clue what it is they are doing with other peoples lives.