Maybe this isn't the most productive advice, but what I can emphatically say is that you need to stop thinking so much. Just get on your bike, and ride. If you get tired? Stop for a while. Start going again when you feel like it.
Don't try and stick to too close of a schedule, or route, or waypoints, but most importantly just don't worry about anything. Figure it out on the road :)
(I will also say that AAA WILL help you on a motorcycle, as long as you have their +RV membership, for $87/year. They've towed me three times on my bike so far.)