If you do end up flying and riding, as others have stated I-95 would not be a good choice on the Ural. Especially when it drops to 4 lanes in SC from GA. I have driven and ridden it and it is not great. I am surprised at how many times there are accidents for seemingly no reason.
I have taken a route on my KLR from Orlando to VA Beach, VA. It totally avoided I-95, was scenic most of the way, and had plenty of opportunity to stop with plenty of fuel stops.
If you want even more scenic and have some extra time, stay on 17 and ride closer to the coast.
Based on the number of miles and your comfort level, give yourself 3 days (2 overnight stops). If you are comfortable and can go more miles, it can be done easily in 2 days. I did it in a day on my KLR, but I probably would not again because I spent quite a bit of time in the dark.
The only issue I had when taking the backroads routes were a few areas with heavy logging truck traffic. Though, if I were on the Ural it would not have been as much of an issue since I would be riding slower anyway.
When I attempted my fly and ride, I found that some states will issue you a temporary tag even if you are an out of state resident if you just bought the vehicle in that state. The cost was low, but, it required the seller and buyer to be there and during DMV hours. That didn't work for me since it was New Years Day.