As someone who has lived in Winston for the last five years (and am now an anesthesia resident here), I can assure you that Winston is not a "pit." Unless, if by pit, you mean the most affordable city in the country with a top 15 program, then yes, it's a pit.
Winston is NOT for everyone. If you are looking for a big city feel, it's not that. It never will be. Plenty of outdoors stuff to do. Charlotte is 1 hour away. Can go skiing or to the beech from Winston for a weekend. Smaller city, yes. I also own a 3BR, 2 bath house 1200 square feet with a yard and a garage (end of a cul-da-sac) for <$650 per month with ZERO down. Kind of tough to beat that anywhere else for the quality of training you would receive at Wake (doing a fellowship in regional, OB, or Neuro from Wake is a waste with the amount of experience you receive in those areas). The pain fellowshp is exceptional, and the peds and CT are getting stronger (and are already quite strong) every day.
Is there a heavy night-life/clubbing feel to Winston Salem? No. But if you want an affordable city with enough to do during your free time with exceptionally good training, then Winston might be a perfect fit.
IMHO.