Mega, have you posed this question to Steph, the SDN mod for Radiation Oncology? She's an SGU grad that did her rad onc residency at Hopkins and is now on the faculty of Brigham and Women's hospital for Rad Onc, if I remember correctly. I ran into an Albert Einstein Internal Medicine resident last Summer at a wedding and his attending was a Caribbean grad. However, I think the situation for FMGs getting into highly competitive residencies was very different at that time (i.e., not quite as competitive). I don't know what the outlook for Carib grads getting into academic medicine is now, so take these anecdotes with a grain of salt.
If you're really determined to get into a US MD school, drop me a PM and I can get you the scoop on some postbac programs with strong linkages.
Also, be aware that while there are many FMGs in academic medicine, it seems that there are considerably less Caribbean grads. It might have to do with sheer numbers, it might have to do with the fact that some of the major Caribbean schools aren't as old as some of the other foreign medical schools, or perhaps stigma plays a major role. (Pure speculation of course)
I would also *think* that your residency performance (and fellowship performance if you do that too) and post-graduate accomplishments (e.g., research) will matter more than the med school you went to. But like I said, stephew in the Radiation Oncology forum could give you a better answer. I would shoot her a PM if I were you.
Good luck