Why does it have to be such a big deal? I drove the Alcan twice by myself, once with an aging 100,000+ mile Honda Civic wagon with my 5 and 7 year old kids. On the way back I had a 100,000+ Honda Accord wagon with the same kids then 12 and 14 years old. There are gas stations and restaurants and hotels spaced out well enough along the road. The road is mostly paved and while there are a lot of frost heaves,the worst thing that happened was the bike rack on the back of the Civic jumped off with bikes attached, but that was easily enough remedied by putting it back on. Our bulldog ate our Kentucky Fried Chicken we left on the dashboard when we were getting gas, but that was our fault. I did have to replace the windshield at the end of the trip both directions, but it was beautiful and a wonderful adventure and we even saw bears along side the road.
I would not hesitate to do it again.