I'm kind of in the same boat as you. I applied this year, had three interviews and now waitlisted at 2 schools (where there is little waitlist movement). I know the weaknesses (which are things I CAN control and easily changed), and applied to numerous Special Masters Programs. When applying I applied to a wide range of schools (practically none in the extremely competitive areas except for my state schools). If I do choose to reapply, I'd apply for matriculation in 2006.
I haven't made a decision yet since I haven't been accepted yet (I didn't apply until late May, I still need to call my interviewer and schedule an interview, and hopefully after talking to him and hearing from the school my decision will be easier to make).
I really think you should evaluate your own reasons for going to the Caribbeans, and see if the pros definitely weigh out the cons. Everybody has different scenarios/situations to deal with and it may or may not work for you. I've evaluated my reasons and listed them below, and hopefully you can do the same for yourself.
I only applied to SGU and leaning more towards it because of an affiliated hospital is located in my hometown. I hope to do as many rotations as possible there and if things work out well, even do my residency there. I've already decided I'd like to settle down in my hometown after finishing med school and want to work with the underserved communities in my county, thus doing rotations and residency in my hometown will give me a jumpstart and establish connections to reach my future goals.
In my case, I'd be saving two years of my time, and if everything goes as planned, I'd also save money during rotations/residency. Since I'll be done two years sooner, the potential income I'd make in those two years will exceed the extra costs in going abroad (or even less considering the costs of some private med schools in the US... AMC is over $40 K a year in tuition!! and I'd be saving money spent enrolling in an SMP and reapplying) I'm 90% sure I want to do primary care, family medicine and/or pediatrics. Since I want to work in underserved communities I don't think they would care where my degree came from, as long as I do a good job and treat their ailments.
I didn't apply to DO schools, but considered it and realized it wasn't for me (I love the philosophy behind osteopathy, but because of my own future goals and the groups of people I want to work with having and MD is better for me).
As for the cons, the living conditions in the caribs, the extra costs (which I've discussed how it's balanced out in the long run), the extra travelling, all the "red tape" with rotations and residencies, lack of support and subpar advising/support services (compared to US med schools).
Thus, as you can see in my case the Pros definitely outweighs the cons. To all other viewers of this forum, if I have left out any "Cons" in my evaluation, please let me know so I can re-evaluate my situation.
Good luck to you and hopefully, my scenario and evaluation helps you in making your decision.