Partly the reason I asked is I'm curious who might be interested in a drag-race from Sarasota to Key West. Its approx 170 nm so it would be better to start the race right as the wind shifts to the NW after a frontal system moves through. That might mean starting in a good bit of breeze.
I'll be there since I have a place to stay in Sarasota and my modified TheMightyHobie18 should keep up well enough, if I don't have a real boat by then or can somehow convince Chris to take the N20 down (yeah right). I'd recommend a 2 day event if we can find a stop over point.
Look at the GT300/Tybee 500 race rules. Basically they go in anything, its the Skipper/Crew's decision whether to go or not go, not the PRO's decision. They'd probably cancel in hurricane/tropical storm force winds, at least I'd be towing my boat and hitting the tiki bar at the next stopover, given I broke 1/2 my boat in conditions that were <25 kts of breeze the entire week.
