I think the PGY2 and 3 classes might be a little tighter than the 4s, maybe that had something to do with it? Regardless, wherever you go you'll be thrust into a program with a bunch of strangers, and the lot of you will have to collectively decide how integrated you want to be as a group
With regards to Gainesville, depends on what you are into and what you like to do in your spare time. Salsa and MMA are pretty big (Ive done a bit of the former, none of the latter). If you are more outdoorsy there's a ton of stuff. The music scene is ok, there are actually some pretty good local bands. I go to a concert a couple times a month, and since alot of groups originate from Gainesville/Tampa/Orlando, you do get headliners coming back to tour their old stomping grounds, but obviously you won't get big names like in a major city. There's also a pretty big punk scene with an annual festival the week for the Florida Georgia game (in case you are so inclined). There are no good indie theaters/art houses; the closest thing is the Hippodrome which has a limited selection. There are three microbreweries in town, and they all have great events on a regular basis. Football is pretty big, regardless of how our team is (or isnt) doing. Medicine holds a tailgate for every game, and the PD goes out of his way to try to make sure people can come, so it can be pretty fun.
As you pointed out, for better or for worse we are 1.5 - 2 hours from three decent sized cities (Orlando, Tampa, and Jacksonville/St Augustine), and people do frequently go out of town for weekends or even day trips (everyone has a car, a car here is a must). You get a fair number of two day weekends, and there is a crazy amount of stuff to do between those three cities. I also sometimes pop up back to NYC (its annoying to have to drive to Orlando, but its a quick cheap flight). The big thing though is cost of living. Despite what anyone tries to tell you, residency pay scale does not scale with cost of living That's true for both ends of the spectrum. The cost of living here is so dirt cheap you save alot of money without even trying, and if you have no dependents you can do pretty well. So the flip side is when you do have free time, you can spend money on airfare, skydiving, festival tickets, theme parks, scuba, whatever. I have friends still in the city doing residency, my preference is definitely to live in Gainesville, go up to NYC and spend freely whenever I want to, then to be perpetually cash strapped. And you still have a decent amount to put towards loans. But your finances may be different, and at the end it comes down to personal preferences
Edit: Being University of Florida, we also have a golf course on campus. Im terrible but if you get a few people together its a pretty good time .
