I'm not sure if I totally agree with you. I think the real key is to make everyone feel welcome. Surely anyone with any type of performance boat that is gonna enter a run would be at least somewhat knowledgeable about the participating boats and what to expect, wouldn't they? It seems unlikely that they would just decide to join a run without knowing the deal.
Grass roots is exactly the type of events that we put on with Ft Myers Offshore- our philosophy from the beginning has been that it doesn't need to be a big production. Just get out and have some fun. Our run this weekend is the first one ever that will require paperwork of any kind. For liability reasons, we incorporated as a not-for-profit LLC and now require membership in the club to participate in the runs. To deal with the issue of smaller boats, we split into two groups, and so far it has worked out fine.
I guess my point is that it can be done, and I imagine others are doing it, too. Maybe some of the big runs have become so big that people are intimidated by the sheer number of heavy hitters.