Winchester used to be a nice place, but between some very violent crimes that have taken place, a rampant drug problem, the city is run down, and downtown has so many prostitutes. The local government seems unwilling to correct any issues, many times it seems they are oblivious to the fact all the cities around them have had good growth while winchester dries up. They have an applebees, and a walmart, Halls on the river took a big hit from health department. There is nothing to see in winchester/clark county, there is a movie theater that wont take credit cards cash only, police set outside of it to watch people hanging out. The town has alot of government housing, but it isn't policed very well. I would suggest if your looking to move to this area, try Mt Sterling, Richmond, Paris Or Lexington. You can get houses cheap in winchester but thats because anything you want to do you to go out and enjoy life you must leave the town. I would say when the old people of the town pass on the city will be overtaken by drugheads. My guess.