I know a few people who did years and matched the next year (after matching unsuccessfully during 4th year). I also know of at least 2 stories where it took 2+ years, with one of the guys doing I believe 1 research and 2 prelim years or something like that.
The outlook was never great for anyone trying to match ortho from the caribbean and with how competitive it seems things are getting and the new schools that have opened up, it iwll likely only be even harder. Anything, in theory, is possible. However, realize you may be in for a long path.
Not sure that this is necessarily truth, but when looking for research years, I'd advise not going to one of the big name places who always advertise here because they will never take you afterwards even if you publish 20 papers for them, unfortunately. It would serve you better (if you go that route) to find a smaller program that has mostly kids from lower - mid-tier US allo schools so that you can put in a lot of work there, get to know the faculty in the process, and actually have a small chance of matching afterwards, instead of a 0% chance.