Hi, I'm the guy who rode the Cannonball on the Blur in 2006. I also rode the first (recent) one in 2004 on a Vespa GT200. A little brief history. My original idea was, in fact, to ride the '06 Cannonball on a Buddy. Genuine offered the Blur, instead, and off I went. I still would like to do the Cannonball on a Buddy, particularly now that a 150cc version of the Buddy is in the works. I can't do the 2008 Cannonball so I hope you (or somebody else) will do it in my stead.
The Cannonball is, for your purposes, a reliability run. You won't be able to keep up with Fuel Injected, water-cooled 250cc scooters. You'll be riding because you have a burning urge to prove that you and your Buddy can do it.
Are you still with me? Excellent.
Since you won't be trying to burn rubber, you will have the added advantage of running a stock machine. I say, "advantage," because all of our experience with auto scooters on the Cannonball leads us to strongly believe that performance variators and CVT belts will not stand up to the rigors of 3300 miles of abuse. In fact, no offense to anybody, but it looked to me like some of that performance junk hardly made it from Portland out to the starting line at the coast. On the Cannonball, reliability is everything.
If you know how to swap the variator belt on your Buddy, feel free to carry one. I'd be more inclined to install a brand spanking new stock belt (regardless of how many miles your current one had on it) just before you leave and not worry about it. I'd be much more concerned about rear tire life than the CVT belt.
Big question: How many miles do Buddy rear tires last? If you put a new one on, will it last 3300 miles??? If not, plan on a tire swap somewhere along the line and build that into your schedule.
You'll have to do an oil change along the way. Keep it simple. Buy an aluminum pie pan, drain the oil into that, replace your drain plug, pour the fresh oil into your Buddy, pour the the oil from the pan into the bottle your fresh oil came in, throw the whole oil-change rig away and be done with it.
A small windscreen, the smaller the better, is a giant help and may actually increase your top speed, believe it or not.
Carry one spare of every light bulb on your scooter. Because you will be a bit slower than some, you may end up riding after dark.
Something different this time that you need to know. On the first CBR, we had one support vehicle. It turned out to be too much for the truck and the two-person truck crew. On the second CBR, we had two support vehicles and it turned out to be too much for both trucks and both support crews. (One marriage came out of it, but that's another story

) So, this time they have decided that it will be every man for himself. This means that you need to start making friends if you want to find yourself a support vehicle to attach yourself to.
To save weight, I chose not to carry enough clothes for the whole run. I carried enough to get me to Iowa and hit a K-Mart there for a bag of fresh socks, underwear, and even jeans (my old ones were shot, anyway). That saved precious weight and space since the 2006 rule was that we had to carry everything on our scooters. I don't know how this will pan out in 2008. You'll have to work this out with whoever you team up with for support.
Good luck!
Feel free to contact me at jrsjr57 at yahoo dot com with questions. I'll be happy to help any way I can.