If you are a college freshman, do things right from the first day and get into a top US school. Do research, do community medicine, get the full experience before deciding what kind of medicine you will be doing. I think with this kind of experience and opportunity, being a doctor is great. But you will have loans and a long education to get through.
In the Caribbean, you still have those loans and long education but none of the benefits of a US education. Plus you are fighting an uphill battle getting a decent residency sometimes.
My conclusion? I think it is well worth being a doctor through a US school. In the Caribbean schools, not so much.
The glass is neither half-full nor half-empty: it's twice as big as it needs to be.