If you haven't read the book The Driver by Alexander Roy give it a read. I think he still holds the coast to coast record and won the 2005 Gumball. Talks about a lot of logistics and planning. Large support team. Even used a plane for part of the race to scout police. It is a good read.
Bullrun and the $50,000 Bet | Gas Monkey Garage
"The Bullrun Rally has been described as the most glamorous and high profile “luxury lifestyle” automotive rally where up to a 100 cars embark on an epic seven-day rolling road-trip, partying in a different city every night.
I’ve won it twice. For me, it’s not about the glitz or glamor – it’s about driving how I live: fast and loud.
At Bullrun 2007 Dennis Collins and I broke the New York to LA Coast-to-Coast record held by David Heinz and David Yarborough set during the 1979 Cannonball Run. Here we are making a $50,000 bet that we’ll break the record."