I'm 58, so I haven't been able to pass as a kid for some time now, but I still act like one sometimes.
There are two things you might want to consider before planing on staying right at Deals gap, first off, it's the place that everybody figures on staying, so unless you are willing to book your rooms in advance, you probably won't find an opening when you get there. Both times I was there, it was booked up. Second, the only food they have available right at the gap is hamburgers french fries, and chicken sandwiches. Any decent restaurant is about a 40 min (one way) ride.
All of the small Cities in the area are geared towards tourism, so finding a motel shouldn't be a problem.
Staying in the same room, and heading out in a different direction every day has it's advantages, like not needing to pack every day, and carry everything along with you, but moving to different motels every other day would open up more riding areas to you. Just something to consider.
One of the roads in the area that I have yet to ride is the Blue Ridge Parkway, and from what I hear it's a good one. From Deals Gap, it heads north towards DC, and from what I hear, it's a long days ride to ride it up & back in one day.
I'll check with a buddy of mine that was down there last year for the name of the place he stayed, as I recall, he said something about it being only $40.00 a night, and it was clean & quiet.
Thurdburd is definitely right about there not being any bad roads in the area. I love twisty roads, and after a full day of riding in and around Deals Gap, I actually got to the point where I was looking forward to straightaways.
tricker, if you want to go on this trip, my advice is
just do it. If I'm on the trip, don't worry, I'll stop as often & as long as you want. I'm a firm believer in riding at a pace that everyone is comfortable with.