To be clear: I wasn't saying they need to open up the checkpoints to make them stop-n-goes. I was only pointing out what is working for the Watertribe events. Their checkpoints are in very remote locations and there's no chance the various checkpoint facilities could support 20 vessels, let alone 100, and the associated people. It's a different type of event in that regard. You take food and shelter with you so you can take care of yourself in the remoteness. That's not possible or practical for a sizable fleet of catamaran sailors on the east coast of Florida. The fleets in the Watertribe were built out of personalities who kayak and tent camp for recreation so it is natural for their events to be structured that way.

Racing up the east coast of Florida in (mostly) well populated stretches of beach lends itself to structured checkpoints...it might be tough to do it any other way for teams. Imagine not knowing if the conditions will support a 120 mile day? You probably won't be able to find a hotel when you do eventually stop...and you certainly aren't going to be able to pop a tent on the beach or sleep on your trampoline with a reasonable expectation of not getting disturbed or in trouble.

I think structured starts every morning is a good way to go for this event. It makes it easier for the non-experienced to get involved. Keep it simple until the next evolution is obvious. Maybe an all out get to the finish as fast as you can may be an option that draws out a sizable facet of our sailing fleets (I kinda doubt it) but we won't know until we get something started. Above all, make the event about having fun and the seriousness will grow within.