It sounds like the Round-Up benefits three groups: FoMoCo, Dealers and Owners. Now I don't know which order takes precedence but if Ford threw in some more change ($$, it is still advertising right?) and the owner's threw in some change (though not a lot since you already received our $50K), then maybe the Raptor Round-Up avenue could open up a little more.
Since you have two top-10 dealers in FL you could have one there, have those two dealers onboard, make it a two day event with one day being a ride to/through Daytona Beach. The last I heard, but have not checked, you could still drive on Daytona Beach (this could be a could or bad thing, depends on the responsibility level of the Raptor owners). The second day could be held in some public offroad area, I don't know of any since I do not live there.
It's stil a 10+ hour drive for me to get to Daytona so it is not in my backyard.
If none of this works then maybe there should be a location poll placed on both Raptor forums in order to find out where your Raptor owners are at, and not where your top dealers are.
This is my last stand, my last idea, my last attempt to have more Raptor owners included in a Round-Up.
Thanks for your time.