Found out a few things:
If you have been arrested for anything; including DWI, you cannot enter Canada for 5 years after the end of your punishment. That is an issue for me right now. You can apply for a waiver but it is a bit involved.
It is impossible to drive to Alaska without going through Canada. As a result of the above I looked into the Alaska Water Highway. You can take your truck/trailer/RV on a ferry from WA State to Alaska for a reasonable amount. I think it will work out OK when compared to time/money/hassle of driving through Canada.
I plan to begin work on the waiver with the ferry as an option. Ferry needs to be booked-paid for 6 months or so out as it fills up quick.