Toolie,
Our trip from NY to AK took 8 days. I could have not stopped(MOA, Cabelas, Whitehorse) and made it in 6 days min. Those are long days pulling a TD. The only tough parts are near the end when you get frost heaves.
The drive would be a big expense for only 2 days in AK. I would highly recommend getting there some other way.
Heres a suggestion. If you can get the car/TD by rail to Jasper Park it would be a great drive up and give you more time in AK. You could fly & drive.
Our trip was 5 weeks and I felt rushed most of the time. That kind of took away from the trip of a lifetime feel. I will go back. Maybe in 2008. Have to finish paying for the last trip.
Go its awesome! -Ray