I was very impressed in your videos by the way you organize stuff using a hierarchy of folders and lists. For the large number of items you have, there really is no other way. Very nice concepts which I suspect took you a while to figure out. I may not do quite as elaborate a system.
One thing I did notice on your maps - the number of curvy roads, compared the the rather strong grid here in Southern Ontario. We must be hugely more flat. Which is good for a farmer, not so much for a rider!
The latest version of Basecamp has the Curvy Road feature, as does the NAV V. In Basecamp, I have made 3 profiles based on Motorcycling to do routing based on the traditional Faster, Shorter and now Curvy. That produces quite different routes for me and I will need to experiment more. May try a Curvy plus no main highways, no interstates combo and see what happens.
Anyway, thanks to your videos, I will be using Basecamp from now on.