Sitting here from my lame desk, I see three ways to do this race:

1) The way it has been done in the past, proper organization, insurance, hotels etc.

2) No holds barred. Everyone starts at the same place and time, finish location is fixed. Run what you bring. Fend for yourself on the stopping, food, sleeping etc. Could allow rotating crew.

3) Elapsed time. Course is set but you run what you want, when you want. Race is scored against the previous record. Again, logistics are up to you/team.

Frankly I could give a piss about cops, fines and insurance. Yes it would completely blow when you hit the beach at midnight looking for a few hours of shut eye and you have to deal with The Man. The real hazard would be a situation where you are forced between dropping the rig, hauling the boat off the beach etc. or heading back out to sea in a nasty blow at night., but those are logistics your team would need to be prepared to handle...