I think I made it pretty clear that you should try to get into the US schools before going to the Caribbean. Graduating from a US MD school will not make you a better doctor, but it will absolutely make it easier to get a competitive residency. However, the Caribbean is not a back door into medicine in the US, anymore than DO school (which is to say, it's not). And US DO may be easier than Caribbean to get residency (depends on the program, really), but not everyone wants to be a DO. I am well aware that DO and MD are essentially exactly the same, but I just didn't want to be a DO. Some people think that's stupid, but it was my decision. Didn't want to have to explain for the rest of my career what a DO was and that yes, I'm a real doctor. I do not believe I'm biased at all, but I am experienced and I know what is and isn't true. You, however, do seem to have the same bias that many other US grads have towards the Caribbean.
A carib grad matching into ortho is very difficult, but not unheard of, and they can certainly get anesthesia, rads, EM, etc. Just taking a look at the Ross match list from 2016, there were 20 EM, over 25 anesthesia, over 25 rads, over 25 categorical surgery, and even 1 neurosurgery match. Again, it is much easier from the US, and I already said that Caribbean should only be considered if the US doesn't work out. But there are an awful lot more qualified applicants out there than there are med school spots and the graduates of Caribbean schools are on par with US grads. Do a little research next time you want to make generalizations.