I have a 2011 Road King Classic I bought new, did a bunch of usual Harley stuff to it (bars, seat, exhaust, cams, tuned it myself, etc) and have around 24,000 miles on it now. I also have 2 minibikes, a Grom and a Yamaha WR250X supermoto that I just put a set of mixed use tires on so it's ok on both dirt and pavement. The best times riding them have been out in TN/NC/PA. The supermoto in particular, riding the tail of the dragon on that was just incredible and surreal, it's such a rewarding experience compared to driving a car. Like Jeff mentioned, if you ride outside of the midwest you get spoiled with the awesome roads available out in the mountains.

I'm semi-looking for a bike that'll go between the supermoto and the Harley. Maybe a flat tracker inspired Sportster OR a hypermotard. Not sure I'm ready for an ADV bike yet.