I have sailed over 100 miles in a day many times. The chances of going straight shot screaming reach to Cuba AND Back are slim. The Gulf Stream can really kick up some waves depending on wind conditions. What will a chase boat do except pick up survivors I have towed a hobie and it is tough in a lake much less high winds and large waves. Towing a hobie slows you down to about 10MPH. Again I would be very cautious even in my 24' Hydra Sport Center Console.
Very few people seem to have ever been around a coral head or streches of very shallow water which is around Key West. I have heard that coral heads and shallows are tough on boats less than the Hobie 21 SE
I waited a whole month in the keys for one good weather day to go to Fort Jefferson.
At least if the race is called off there are great places to drink. World Class Bars that is.
I do think a trip not a race to Bimini would be a better idea. Shorter by 40 miles. More boats in the area. US Coast Guard and Sea Tow close. Much less political problems. The Government of the Bahamas would probably sponser a group of Hobies Search "Bahamas Boating Flings"
Gary Hobie 21SE