You're headed up to some incredible riding, so there are almost no limits, but I thought I'd throw out a few ideas. I did the ride to Fairbanks last year from Milwaukee and back, and I road Death Valley this past fall.
I'd definitely recommend riding through The Mojave Nature Preserve and then Joshua Tree National Park on the way to Death Valley on the way up. Great time of year to be there. If you go, I'd recommend Titus Canyon first and foremost (IF you're ok with bouldery dirt and 180 degree switchbacks). Amazing ride. I did it two-up, so it's definitely doable - just depends upon your comfort.
By hitting that area on the way up, you can enjoy the Pacific Coast Highway (Hwy 1) on the way down in warmer weather. I road San Fran to LA in November, and it's absolutely freaking amazing.
As for the trip up to Alaska, I wrote a blog about our trip last year, and it might point you in a few of the right directions. Check it out, and let me know if I can answer any questions. www.longroadup.com
Happy and safe riding!
Off to Cabo via LA in a few weeks myself. We may cross paths.