On the one hand sailing off shore in a cat that has been sitting on the beach for 5 years sounds sketchy. They use stainless rivets in aluminum all over beach cats. Corrosion can be a problem. Then there is the stitching on the tramp to rot as well.
On the other hand, in the early 80's, when i was manager of the Hobie cat rental at Phil Foster park, The sails were left up one nite by the slackers working that day, and along came a fugitive running from the law. He jumped on one of the H16s and sailed all the way to the Abacos. We got a letter weeks later to come and pick up the boat. The boat wasn't worth it though.

As for a Raid in the Keys. Makes sense, but you would need to pay a crew to set up all those start and finish lines.

Also Mike Worrell sailed the 1000 miles with just the one boat the first time. Later on,i think it took 3-4 days non stop, except for checkpoints, for the 3 man teams to finish the 1000 miles on H16s. They would rotate the third man in at some of the checkpoints, and the turn around took seconds to complete.