We did the TOW in June 2016 from Dawson City. Few things not mentioned - there is a 10 minute ferry ride across the river to start the highway. Our timing was bad, behind a caravan, and waited about 3 hours to start. Don't sweat the small stuff...
As mentioned, weather will impact the road, it was nicely graded, safe, stress free to the Border. On the US side as approaching Chicken, the road was in heavy use and quite muddy. Slow and easy, no issues. A night in Chicken was a hoot and the drive the next day into Tok was good.
That experience was certainly a highlight of the trip. Remote, yet comfortable with the roads, beautiful scenery, true sense of being "out there."
Once in Tok, it did take a good hour with a pressure hose to get the top layer off the truck and trailer, but no other worries.
Take your time, enjoy the journey, don't sweat the small stuff...
Dawson City also was pleasant as well. Glad we did it.