Just a couple of notes: it's dangerous to go to a school based on the assumption that you will do well and transfer. Law school grades can be unpredictable. You might end up in the middle of the class unexpectedly. Don't go somewhere from which you wouldn't be satisfied graduating.
I think that going to a Florida school would give you a better chance of finding a good job in Florida, since it will give you the opportunity to build contacts in the legal community while you're in school. And I think taking out a few loans is okay, but for three years at NYLS, even living rent-free we're probably talking about a good $150k-$160k. After taxes, I think that comes out to $2000 in student loan repayment a month (this is based on a rule of thumb that I was told about where every $10k of debt equals about $125 a month in loan payments; obviously it varies a bit based on prevailing interest rates). Are you comfortable with that kind of debt?