First - Welcome. First, 2nd, third and fourth post on the forum.
Say this a lot for those adding load into the bed and towing. Adding a simple pair of Timbren bumper stops will help handle the additional suspension load with the bed loaded and trailer tongue-weight added.
Aggressive tread on different tires just might be real useful. Snow can get deep and the roads, from my summer motorcycling experience, can be hard to even follow at times, especially if snow covered. There will be snow in winter and long stretches of "nothing" to go with it. Use treated fuel and carry some anti-gel also to supplement in case the temperatures get -20*F or lower. They probably will. Don't forget warm clothing and coverings if delayed outside. Places to shelter are sparse in some areas. Consider a spare fuel container if delayed and some drinks and food also. Communication is sometimes broken at certain spots so figure you might need to take care of yourself if need be.
Reads like an adventure. I say, go for it.