My wife would love the comment about Charlottesville city council. I have had to walk her away from the TV set local news on MANY occasions based on what goes down in C-ville. Albermarle county leadership is not too far behind.
We live about 20 min west of c-ville on a mountain and love it.
That being said- living close to c-ville,but not in it, does have it's advantages.
As for South Boston, Danville, Martinsville, etc.. I would strongly suggest visiting those areas prior to committing.
Lynchburg is larger, and most of it's money comes from Liberty University- again, I would spend time there to to see if they are right for you. All four of these towns were early-mid 20th century towns, got bypassed with the major interstate system, and have been somewhat left behind. Although there has been some revitalization, these are not uber hip yuppie places full of young vitality.
Also.. +1 for Lexington. I would check out Staunton Va as well. nice downtown area. Good theater. Good food. If you aren't raising children and like beer, wine, and good food, research Nelson county Va. 151. I think there are over 15+ wineries/breweries near where I live all within a short drive. It's easy to become a food snob quick out here!
Lot's of good music in area.