Thanks to all of those who have replied. Even if this is an oldish thread, I still check in from time to time.
So I actually applied and was accepted for transfer to a Caribbean school (not top 4, but soon to be part of top 5...any of you who know the Caribbean situation will be able to figure out which school). The school has been really good to me, understanding of my situation, and they gave me credit through half of 3rd year (24 out of 48 weeks of cores), which I thought was a pretty sweet deal.
I recently started in my rotations at my new school, and there has been a little bit of adjustment, but overall it's going well. Most importantly, my new classmates are really great - it seems the admissions department here really knows what they are doing. My colleagues have been incredibly welcoming, and I hardly feel like "the new kid." It's the first rotation for many of them, and I sometimes find myself teaching them things I've learned from my previous clinical experience, which they seem to appreciate.
I lined up a couple of away electives in my field of interest, hoping to make that connection and secure a match spot (or at least a great rec letter). I know it's going to continue to be a tough road, and that the match isn't the virtual guarantee that it was when I was at my previous school, and hopefully this will go far as to helping my chances.
There are times when I really miss my old school (and to think about how my old classmates and I used to trash it), thinking about what I should have done differently or where in the application process I might be. But when I go to interview and examine a patient, present an assessment and plan to the attending, discuss an exciting case, or help a classmate come up with a differential diagnosis, I forget all about that - I feel good about myself and remember that this is really what I love, and that staying the course has been the right decision.
BTW, someone mentioned this before, but with regard to the debt it has been pretty manageable with the new income based repayment (IBR) program. I also intend to take advantage of the Public Service Loan Forgiveness program for my previous school's loans - the private ones for my new school aren't so easily managed, but hey, gotta do what you gotta do...