When are you going to do this? I live in Omaha, one mile off of I-80. I think I may be right along the way. With driving through the Midwest, at least parts shouldn't be a problem if you break down.
It sounds like you could ride the bike out, and load it on the back for the return trip. Although, that would be a long ride for both a 350 Honda, and a '50 big bolt. But if you got the time, that would be a trip to tell the grand kids about.
John