I'm happy you have made it through so far but knowing what you know now... the question is would you have gone to the carib if you could do it all over again?
Also, did you go in KNOWING what residency you wanted to enter?
I honestly feel that the amount of effort you guys put in to land an IM or FM spot would have somebody in the US land something more "competitive"... like rads, EM, hell... even general surgery. Not saying IM and FM are cakewalks by any means but it is what it is.
I've seen the board scores you guys can put up... as the fifth semester scene gives you guys A LOT of material and time to prepare than an average US student here gets.
Glad it is working out for you so far.