Change the air in the tires as soon as you get there from the American PSI stuff to the Kg PSI air found in most foreign countries.
I would change the stock front tire right now over to a better one than the death wing and load both front and rear tubes with Ride On balance and sealer fluid.
Where you are going and the accessibility to fresh fuel will be important in this adventure. I would have a rear Cycle rack for sure on the bike before it travels and of course a DID X ring chain on new sprockets.
The major problem with doing what you are doing is in the details. You can bring all the spare parts as noted above but going strictly by Murphy's Law, the part that fails will be one you never considered. TWs are a very reliable bike but at any time a "Watch A Ma Call It" could fail and leave you stranded. I would be highly concerned with the fuel system and the types of fuels you will have in foreign countries, Real gasoline or will it be E-10, E-15 or some other ethanol blend these bikes were never designed to run with. I think I would want a brand new carb in the box along with the boot from the carb to air filter box because a very high percentage of the issues we hear have everything to do with the fuel delivery system.
Wishing you much luck and can't wait to hear where you are going and hope you keep us updated along the way.