Thanks for the links, I've been pouring over historical data from the Fisheries and Oceans sites and buoys for some time but I hadn't been to the shipwreck site. In all fairness, I managed to find a few sites focused on Shipwrecks of the Florida Keys that documented its fair share of wrecks itself. You obviously have a healthy respect for the sea and I respect that. I expect considerable skepticism over this event as being "over the top" and risky but I firmly believe that systems can be put into place that can minimize the risk to those involved. Make no mistake, there will be plenty of risk no mattter how well one plans.
Keeping the event small would allow a few suitable chase boats to keep close enough to each team to render effective assistance. Today's navigational and satellite aids can pinpoint waypoints as well as boats in distress within meters. Handheld VHF & GPS tracking, cell phones, drysuits, favourable prevailing winds and the proximity to land offer some security on this race as do the significant water traffic from tourism and fishing. And don't forget the powerful tool that we have with the internet allowing our community forums such as these as a venue to share their experience and insite thereby leaving no stone unturned in making this as safe as possible.
But yes, these positives also tempered by the inherent and significant risks such as 325 miles of open ocean to one side, and desolate, rocky shoreline on the other, 70 miles of shoreline that has no road access, significant currents, tides, deadheads, whales, uncharted rocks, no wind, too much wind,..the list is endless. How do we handle a serious breakdown that disables a boat 2 miles offshore but 40 miles from the nearest road? How do we effectively scout the bail-out sites if things go awry on the ride down the outside? Yep...there's a lot to consider. Again, these forums I'm certain will shake out many other risks but also, solutions.
In response to your question, "I am confused, tell me again what is so appealing about sailing around this island that outweighs the rocks, the current, the freezing your ass off water, and the typically crappy weather?", my answer would be the classic, "Cause it looks like it would make an incredible adventure those fortunate few that take part in this event."
Thanks again for your comments Mike. Keep em coming.