Before applying for residency, you must plan things through very well to the exact detail. You must be realistic and you must also choose a path that you love.
What I noticed ever since I graduated is that throwing your interest at all directions isn't the smartest move. If you want Internal Medicine, then do anything and everything to get yourself there, if you want family then get yourself in Family. If you want to get into a competitive then work hard to get in. Don't let the fact that you are from a Caribbean Medical school get in the way of getting into a residency of your choice. Currently Saint James students are getting into Anesthesiology, Emergency Medicine, and Surgery. Other Caribbean medical students are getting into other specialties as well.
At the end of the day, follow your passion, and work towards the medical specialty that you can see yourself doing for the rest of your life. Whatever you do make sure you give your 100% and don't look back. When you follow your passion and not the money, then you will see that the money will come and you will do something you love.
Research as much as you can on what specialities interest you. If you have time after graduation, then volunteer at different specialities to see first hand which one catches your attention. The reason I suggested volunteering because you may not get the same feel for it as a medical student when you were rotating.