Medved, what things interest you about Asheville? I live in WNC. Visit AVL from time to time. Love the trendy restaurants, Biltmore Estate and Village. Shopping is just like any other city.
I live higher up, so I view the winters there as kind of warm. Currently, AVL is a warm 25 and we are sitting pretty at 17.
I would live in one of those small towns 20 minutes from AVL. Looks like plenty of housing stock. Do you want a no maintenance townhouse? A 2 car garage in a development kind of house? A mountain estate with no one around and views?
We like (in no particular order) living in a smaller city but still with lots of stuff to do, a walkable downtown, great restaurants, lots of independent (non chain) businesses, excellent beer selection and bars we enjoy hanging out at, beautiful scenery, lots of great hiking opportunities without a long drive, the farmers markets, the slightly "off beat" environment (especially in West AVL but certainly other places too), Southern breakfasts, the coffee shops, hidden terraces to have a meal or a drink, some local educational opportunities, mostly friendly people, lots of people "from away" so we would not be unusual, the River Arts district, a very civilized airport, and a "live and let live" environment, where people tend to respect one another and get along even if they come from very different backgrounds -- or at least more of that than where we come from.
In terms of housing, we would like to be close to commercial activity -- ideally walking distance, but that is not essential if there are compelling trade offs, such as very nice views. A big enough house (at least 2500 square feet) that is relatively quiet and in excellent, renovated, modern-on-the-inside condition. I like Montford. Wife likes East West Asheville. We have looked in some other neighborhoods too and we are flexible.
The small surrounding towns seem very nice. I liked Weaverville, for example, But coming from urban areas I think we might be better off more close in. We will pay more for that, but we are OK with that.
We would likely leave for at least a month every winter, to go someplace warm.