John,
Though we try different routes each time, still catching up with family and friends along the way, we have yet to drive the Dempster. If we did, I'd leave my trailer in Dawson, or at yukon river park, and sleep in the truck. From what I have heard from conversation, that road, past eagle, can be a real tire shredder. I'll deal with four tires... not more.
Up to tombstone, in decent weather is easy... so i hear. People I have met drove up and back, in passenger cars.
Maybe someday. As we've driven most roads, already .
My favorite Alaska roads are the fifty miles of the Richardson highway, approaching valdez. Those 50 miles are some of America's best views, imo. Lots of great pullouts for overnights. Especially, the 1890something gold rush pass lookout . In clear days, it's just amazing. On crappy days, it's just clouds and gray. And sometimes, snow, early season. . Timing's everything .
Second is the gravel denali highway. Only 100 miles or so, but worth a night or two, if you have the time, and tankage. Lots of beautiful pullout spots to camp.
We spend a disproportionate time of our trip each year in the relatively empty Yukon, and almost as empty northern bc. We find the Canadian roads to be better, gas is of course higher, but the camping experience is amazing.
Sherry