>>893525Sounds like a fun trip.
Go through the bike between now and then and replace anything that's worn.
Make sure everything's 100% before you leave - Fork oil/seals, clutch plates, brakes/pads, air filter, tubes/rim strips, coolant, seals (countershaft, gaskets, crush washers, etc), valves in spec, battery/electrical/ignition system.
I'd also add a tank bag and pull 12v (along with added USB charger) in there to keep your shit charged while you ride.
Plan for tires and oil changes along the way. Cheapest route is to stop by an auto parts store, buy what you need and /diy/, but not all places will let you change oil in their parking lots. Tires, probably worth having the shop you buy from mount and dispose of the old ones. I'd run something more dualsport-street-oriented than a knobbly dualsport-offroad, you'll be a lot more comfortable knocking out highway miles on those. Play with gearing to find a good setup for the riding you're doing - deep offroad gearing sucks for highway miles, and tall highway gearing sucks in the dirt.
Outfit your moto to haul some of your luggage (especially the heavy stuff), and get the suspension set up for that weight. A pack isn't a bad thing, but it'll wear on you after a while. Camelbak is nice, nice to have some storage for stuff when you're off the bike, but get the big/heavy stuff off your back. Fender pack for tools is nice and inexpensive.
I'd be a little nervous about security in "large cities" - motorcycles disappear fast. Cables help, but 2 guys can throw a small dualsport in a van and be gone before you even turn around. Alarmed disc locks can be hit-or-miss, I had a LOT of false-alarms with the xena I had (Ended up pulling the alarm batt out and just using the lock as a regular disc lock).
Dress for the crash, not the ride. Good boots (enduro/adventure boots with good ankle support), pants, jacket, gloves. Armor, either integrated or worn underneath (Knees, elbows, shoulders minimum).