I second MLW's comments. I grew up in Tampa and still visit regularly. Overall, I think the city is a nice place. I would prefer to live in South Tampa or Seminole Heights but that makes the commute to USF kinda crapphy (275 and fowler suck). However, it would pay-off if you did your rotations at TGH or in St. Pete.
There is plenty to do in the city; bars are cheap and open late, real estate is relatively inexpensive both to rent and buy, and there are 3 pro-sports teams. In addition, beaches are close by and weather is favorable. Overall, the city is designed decently with nice public spaces and areas like Ybor, Channelside, and Hyde Park being attractive.
If you consider cost and quality, I think Tampa does pretty well in comparison to the more homogenous and predictable Gainesville. I currently live in a college town (Ann Arbor) and I don't think I could handle moving to an even smaller college town during medical school that is certainly characterized by typical college bars, parties, etc. This could be appealing for some people, but just not for me at this point of my life.
Miami was unexpectedly attractive to me. I spent the entire weekend of my interview exploring the city with my wife and we were impressed by most areas and suprised to find that much of the city is relatively clean (e.g. north miami near FIU, coral gables, bricknell, the groves). In addition, having 4 pro sports teams and plenty of bars-resturaunts are also attractive commodities. However, the nightlife is sooo much more expensive than in Tampa's Ybor city, making it to much of a hassle for me to want to deal with. However, the Jackson campus is awesome - I was very impressed with the hospital, research centers, and medical school proximity to each other. I think that this would make a great atmosphere for a student. The traffic, of course, seemed to be even worse than Tampa, but I suppose the metro rail could alleviate this a bit. Overall, the cost factor doesn't compare to Tampa (both in terms of the city and in terms of Miami's tuition) but the quality factor is pretty high.