Paul,
I can assure you that Asheville's weather in Oct-Nov is quite a bit better than Chicago's. You can expect many 70 degree days well into Nov. and occasionally even Dec.
Asheville is home to four Ross courses-Muni, Grove Park, CC of Asheville, and Biltmore Forest-with Biltmore being the standout (its a pretty stout test as well, with only one par 5) CC of Asheville is solid if unspectacular.
The front nine of the muni is flat with several green complexes that were probably really scary when built. The green of the par 5 2nd must have been breathtaking. The blind tee shot ninth might be the best medium length par 4 in WNC. The back nine occupies much hillier ground and possesses the skeletons of several outstanding holes-and finishes with a 210 yard par 3. Fixed up, the Muni would be the equal of anything in the mountains.
The Grove Park in was renovated by Kris Spence and is well-kept and has some fun holes...but nothing earth shaking...certainly not worth 125 bucks or whatever it is they are getting these days.
Waynesville CC (30 min west) has nine Ross holes in varying stages of neglect and decay. The present 4th green must have really been something special...its a total factory and not worth the drive.
Hendersonville CC is 30 min east and has one of the sportiest courses in the Southeast. Pretty violent terrain reminiscent of Camargo in places. Perfect use of the land and the short 8th (I think it is the 8th) is one of the best really short par 4's in America, for my money. I'll try to post some photos of it someday.
If you can get to Wade Hampton in an hour from Asheville...it will only be by helicopter...same for Grandfather and Diamond Creek. There is no easy way to get anywhere in the higher elevations from Asheville. If you can get on WH-you should really try to play Highlands CC, which is only 15-20 minutes away and the two of those would make one hell of a 36 hole day trip-have dinner at the Lakeside Rest. in Highlands afterwards.
I understand the Cliffs at Walnut Cove in S. Asheville is well above average but I have yet to see it.
Laurel Ridge (Cupp) in Waynesville (30 min) is THE prototypical mountain course and has some really ridiculous holes but several outstanding ones as well (including some magnificent vistas) worth a drive over if you do not have anything lined up for the day.
Hope it helps...