Shorter 'Work The Bugs Out' Trip?
Since you're waiting until this winter to head South, perhaps you might consider a shorter (say 2-3 weeks) trip to begin with to, as DougieB said, "iron the bugs out" of the bike and figure out what gear works for you on the road?
My wife and I just took 2 1/2 weeks for a run up to Prudhoe Bay...we learned quite a bit about what gear is bogus (my poor digital SLR is going on the discard heap due to disuse) and what works well (waterproof roll bag much better than a top box). Plus, it temporarily satiated our wanderlust and held us over until the big departure on Sept. 8.
The nice thing about Alaska/Canada/lower 48 is that you still get the travel experience without dealing initially with language barriers and customs and so forth.
Good luck, and hope to see you on the road!
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