I have a friend running the cannonball for the second time on a 1928 HD JD. I wish I had the time and money to do it myself. It is a contest of man and machine (old one at that) against the world. It will truly test you and your McGiver-ness to get from coast to coast. A lot more challenging than an ironbutt. It is like climbing Mount Everest, you just need to test yourself and your wits to do it. If I hit the lottery (which I only play 2-3 times a year) I would do it in a heartbeat.
I agree - with the time and money (mostly the money) I would do it in a second....