Your post is admirably crammed with hubris and ignorance--basically, you're at the place where we all begin our journeys--even those who sound tough and experienced. It would be silly to start critiquing and quibbling with each piece of your plans. Probably the most important advice at this point would be to try to nurture a bit of humility as you move forward. It sounds like you'll need it.
I'm concerned mostly about your stated intent to take with you a friend who's "terrified" of motorcycles. It's well enough that you're on the steep initial learning curve; this is not the time to ruin a serviceable friendship (much less romance) by overextending. Try to work her into the picture gradually.
Good luck and safe journeys.
Mark
Mark
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