I pull a 33' TT with Dodge 2500 diesel. Total length 65 feet. No problems.
Leave early, I left Jan from South AL follow the Gulf Coast to Big Bend NP, Turned north and follow the snow to Yellowstone etc. Left AK mid-Sept. I carry 20 gl extra fuel in the back of my pickup -- at 10MPG I did not want to run short. AK is ideal for dry camping on the side of the road.
Check your credit cards some charge an extra charge in CA. Some (Chase ?) do not. In any case let the Credit Card company know you will be out of state otherwise they may place a hold on your card. You will need a passport.