Here's an awful lot of info for you to read. As far a road conditions, if you've been to California and can drive on their rough roads, you can handle the Alcan - just SLOW DOWN, don't get in a rush. There are frost heaves and after you bounce all of the clothes off of the clothes rod in the closet once or twice, you'll pay more attention when they mark the frost heaves.
This years Roll Call Alaska 2016Roll Call Alaska 2015There's also a Roll Call Alaska 2014 & 2013, but for some reason I can't call them up.
Some people like to take a caravan tour the first time to figure things out and then go a second time at a lot more leisurely pace on their own.
Alaska Caravan ToursOne of the things I recommend is to drive the AlCan one way and take the Alaska ferry the other way. You can get off in each town, spend three days to a week and then catch the next ferry down to the next town.
Bill