Im wanting to try some of the state BDR rides, at least parts of them (Backroad Discovery Route, dirt roads across the state). Az, NM, and Wy sound interesting. Some sections can be a little sporty, some arent too bad for a bigger bike. Ive been watching some ride reports on ADV Rider and facebook. I need to look up the others you mentioned. They are familiar but I dont know much about them.
Im not likely to do any long sections at one shot, but just getting out in the hills on dirt roads is a lot of fun. I did it quite a bit on my 1947 Knuckle I built. I started from the ground up pretty much and rebuilt all the motor and trans, fresh (used) parts elsewhere with new seals and bearings etc as required. It was pretty trouble free for a few years of cross country riding and all over Arizona. It was hugely fun at the time.
I need the electric start now, but like the older stuff a lot. Im planning an early panhead project bike (48 to 52-ish), but the general riding bike will probably stay the 84. Having a lot of time on my hands, I realized that the 83s and 84s had the VIN number on the left case, so Im planning to swap the right case to a Pan case. I love the looks, but still retain the electric start on the left case. STD made conversion pan heads that drop on Shovel cylinders. If I dont turn up a set of those, theres other options. It would be basically Panhead right half, electric start shovel left half. Not as cool as a complete pan motor, but way less expensive and have the better electric charging and starter, not to mention I already own it. I have a 1950 R case to use, and access to the line lapping tools to set up the lower end correctly.
Im going to wimp out and do short trips on the bike, day rides and overnights, using a cargo trailer camper to haul the bike and stay in for winters in Az. Long ago I spent years living outside and sleeping on the ground most of the time, Im ready for more comfortable camping now. I think I can carry enough sleeping pads on the sidecar rig for overnighters now and then, and stay in the camper the rest of the time.