Say this Dr. Bill individual was in his late 20s/early 30s when he graduated from that Caribbean school and passed all his steps (1, 2 CK, 2 CS) all in one shot with above-average but not rocking-great scores before applying for the match in 2011/2012. Would he have been in a better situation?
I am Canadian will be turning 24 this year and I have a 3.56 cGPA and took mcat twice (got 33 both times) but the problem is my lacklustre cGPA blocks me from the Canadian schools and I applied to American schools broadly once in 2012 (submitted my application in late September after an August MCAT and didn't get one interview- with similar cGPA back then). This year I applied again and I got into a European school (not a for-profit business school) and this thread was a really hard read for me. Are IMGS really looked down upon even after matching (as in stigmatized?). I have a few friends/acquaintances from university and high school who have already taken the plunge down to the Caribbean and will be interested in seeing how they do.
Because of your GPA and MCAT scores, I think it's pretty safe to say that you would be one of the people that does well in the caribbean. If you could handle the lifestyle adjustment to living there, I don't think you need to worry about being able to handle the material.
Whether IMGs are looked down upon after matching is really up to the individual person doing the looking. There will always be people, many of them on this forum, that will always assume you are an idiot because you went to a caribbean school. That said, lots of physicians don't judge other physicians by where they went to medical school, they judge them on their competency. Caribbean grads who finish residency don't have any more trouble finding jobs than US grads, you just likely won't be working at a prestigious university.
That said, there are 2 very real downsides to going caribbean.
1. Majority of grads match into primary care (FM, IM, peds, psych). People absolutely match into non-primary care fields, but these are only the top applicants and even then it is somewhat of a crapshoot. Also, even in primary care fields, you are basically disqualified from top tier programs. You can still get a great education at mid-tier programs and lots of IMGs match into them, but they are your ceiling for the most part.
2. Uncertainty about the future of GME positions in the US. US MD/DO enrollment is increasing every year, and the US congress has not increased GME funding since 1997. >6000 IMGs matched this year and have in past years, so there is really no crunch being felt yet (and I assume there won't be for at least 3 more years). That said, if GME funding does not increase, there will be a point in the next 5-10 years where there are a dwindling number of spots for IMGs. There is also the ACGME/AOA merger that will be complete by 2020, and it's unknown how that will actually affect the number of GME positions.
2a. Being Canadian, it will also be that much more difficult for you in the US match because you will need a visa. Most programs provide them, but I think there is certainly a preference given to US citizens/permanent residents.