I would be leary of Ole Asheboro. Progress has been made and they have done alot to clean up the neighborhood but its still has its problems. Since you are interested in the general area, I would look at the Southside Neighborhood. Its an upscale neighborhood directly north of Ole Asheboro but its like night and day. Lee street serves as a barrior between the two neighborhoods and Southside is a much safer location, its upscale and I did notice a house on Gorrell Street for sale in the Southside neighborhood. Southside has a variety of living options. There are upscale apartments, condos, townhomes, live-work units and singe family homes. Many of the single family homes are new and they are designed to look like homes from the early 20th century. Some of the homes have been there for decades and have been renovated. The homes there are in the price range between $250,000 and $380,000. Some of the townhomes are $500,000. What I like about many of the single family homes in Southside is that they have detached garages that have living spaces above the garage complete with a living room, kitchen, bathroom and bedroom. So you could rent that space out if you wanted to or use it as a guest house. BTW im a Southside resident.
As far as Ole Asheboro, I definately wouldnt be walking alone at night, particularly if you are a female.
http://www.southsideneighborhood.com/