Hey, I thought I'd answer some of your questions... I'm a first year at Wake, and I really love it! If you get an interview at Wake, congrats!!! It's true that you won't get rejected once you get offered an interview. Your odds are pretty good, especially since there is a lot of waitlist movement.
Winston-Salem is a pretty city, but it's small (~150,000ish). It's a quiet, clean city with admittedly not much to do. I'm looking forward to some college basketball action -- it's huge around here. The arts scene here is pretty big. There's the NC school of the arts nearby, and there are always concerts/plays of some sort going on.
One good thing is that housing here is really cheap. But Wake is a great school, with really nice facilities. One thing I really like about the place is how wired it is. Students get laptops because the entire curriculum is on-line.
The med school is separate from the undergrad campus, but it's only about a 10-15 min drive away. As for diversity of population, there is a large Hispanic population in the city, which is why there is a mandatory Spanish course in 4th yr.
Wake also has what's called a Community Practice Experience, in which you spend time with a doctor in a rural community. So, yeah, you will get exposed to small, small-town life too.
This was a pretty general post, but I hope it was helpful. Let me know if you have any more questions!