Thank you for your responses. My original plan was to ride single, but now that there are two, I should probably reconsider using that bike. Maybe buying a newer, more reliable, larger engine bike and selling it afterward would be a better option.
The Hondamatic is a pretty awesome bike, I didn't even know that there were automatic motorcycles before I ran into this one. I was going to sit down for a month and go through a maintenance check: carbs, brakes, seals, cam chain, maybe new tires. However like you mention, LowRider, if something happened to the transmission on the way there, I don't know if most mechanics would know what to do with it or how long it would take to find a part.
I look a 500 ml bicycle ride in Germany, 10 hours of constant peddling and setting up camp wherever we where when it got dark. I fell in love with that idea, so I'm doing it longer distance on a motorcycle. I think it's kind of an instinctual craving for independence and freedom that takes over men(and various women), like a modern day Oregon Trail pioneer. Except I have AAA and they were pretty much screwed if something broke down.
Do you know of any good books/websites/maps that really help out the motorcycle traveler? I'd like to use back highways rather than interstates(mainly because of the view), but I don't want to hit really curved roads where I'm having to go 40mph for half a state's distance. I don't know if there are maps made by riders that know of good travel roads.