Here's a link to my friend Brendan Leonard's trip site. He and a high school friend from Iowa are leaving San Diego Feb 4th to ride to Saint Augustine, Florida. He's posting regularly to the site as he prepares for the trip and worries about what may happen en route.
Brendan is a great guy and a super writer. I am sure that you'll enjoy his pre-trip posts and want to follow his journey across this great land. By the way, Brendan has ridden Ragbrai and used his bike for urban transportation. He has done ambitious day rides. He's a rock climber and camper. But, like most of us, he's never done a ride of this scale.
Bookmark the site and you can do it with him.