I wouldn't expect the roads to improve anytime soon in YT as the money just isn't there for the maintenance needed. As Susie mentioned for many years much of the Alaska Hwy in YT was maintained by Canada and the US provided most of the funding. We are the ones that mainly use the road, not the Canadians. There was for many years an agreement, the SHAkWak (sp), that provided the money, but the current administration in Washington D.C. decided to cut that funding a few years back.
Yukon, is a territory that depends heavily on moneys sent from the federal government in Ottawa, but the political problem is that they already sent something like 10 times the dollars to the Yukon per Canadian citizen that they do to the provinces of BC and Alberta,etc. I would doubt that the politicians in Ottawa are going to be interested in sending even more money to the Yukon, just to maintain a road used mostly by US citizens and companies.
Alaska is much the same in that the federal government is the largest employer in the state. The federal dollars spent in Alaska far exceed the amount the few citizens of Alaska pay in federal taxes and they have no state taxes to speak of at this time. On one hand I doubt that the Washington politicians are going to be willing to send anymore money to Alaska but on the other hand the US military has signed a plan to expand the early warning radar base at Clear (Anderson, Alaska) just north of Denali Park. They are looking at spending about $1 billion dollars from what I have read. A three to five year project, that will bring in 1,500 to 2,000 skilled workers to the area. Not sure where they plan to house that many workers in that area, Fairbanks? build a large camp? who knows? but it will change that part of the state forever.