Why not return it to it's roots, and have it with few or no designated check points, allowing it to be a true "iron man" event. Sailors would have to pick the best times and places to rest (big time stategy decisions). Each boat would have to have it's own shore team following it up the coast. Too bad there's no time on distance handicap system, that would allow for a reverse start resulting in the first to the line winning the event.
This greatly simplifies the running of the event for the organizers. They would just have to fire a gun in Florida and wave a checkered flag in Virginia. The problem MW is going to have with running anything like the all inclusive race/fee type of event like been done recently, is now not many people are going to be trusting him with "up front" money. This greatly limits his options as to what type of event he can run.
Good luck, ML