I'm definitely interested, but have a few thoughts:

1) The first leg is going to be long, no way around it. I spent Monday driving through the north end of the keys, those mangrove forests aren't real friendly for landing on and access is pretty limited. Honestly, I wouldn't make that run without a spinnaker boat (that can also do 12kts + upwind). On the flip side, I'm a fan of the run what ya bring concept.

2) 80 mile days are fine IMO. With the opening leg being close to 100 miles, that would make the event 3-4 days. If you can schedule it over a weekend, that may make it a lot more feasible for teams who have real jobs. Big might, since the islander is a long haul for anyone outside Florida.

I do like Jakes checkpoint idea. That would enable run what you bring, and the faster boats can make less stops (saving time and money).

Might be worth mentioning that there is a ~100 mile distance race in the works in NJ for the June time frame, and a possibility of a 120 mile non-stop race on the Chesapeake memorial day weekend.