ooooh, this brings back memories ! In 2006 my wife and I did a round trip road trip from Portland area to Alaska. We were ground-tent camping ! Yep, set up tent and broke down every day. I had a sabbatical from work, it turned out we were exactly "40 days and 40 nights" on the road and we covered 8k miles. Awesome trip, I've been wanting to do it again ever since. But not ground-tent camping next time ! My wife's brother lives in Wasilla, AK, so we finished up there, although we went up to Fairbanks and did a bus tour up the Dalton highway. I forget how far we went, but it was an out and back in one day. It was tedious in the bus, we should have driven, although we were a little put off by not having a CB radio and being in a rental Ford explorer that time.
So many stories from that trip : I 'll share one : leaving Alaska we took the Taylor highway across to Chicken, heading for Dawson City in the Yukon. There was a little place along the way where we planned to get gas. Dude didn't take credit cards, so we were out of luck, not having any cash on us that day, with < half a tank left. So we cross our fingers and drove on, the gas gauge falling and falling. I remember the last 8 or 10 miles was all a long down grade down to the Yukon river at Dawson city so I put the car in neutral and coasted the entire way ! Somehow we made it to the ferry with the tank reading Empty, and across the river and into Dawson city, where it was a case of "any gas station will do, I don't care the price" !
We also came back via Jasper / Banff and Glacier NP. Didn't drive the Dempster highway though.
I'll have to do that trip again. My kids are 11 and 14 now, they would enjoy a road trip like that.
If your trip comes together, you should let me know when and where you're coming through the Peoples Republic of Oregon, I'd love to see that rig of yours !