If you would sponsor an assembly in the City of Cape Coral, Florida, and if more than 500 people are likely to attend, then you need a permit and insurance. From Cape Coral's POV, this is reasonable. For an individual simply encouraging people to speak up about the behavior of their general government, it's a bit much.
Perhaps there are parallels here to the Tea Party of December 16th, 1773. In that case, the demonstrators did not petition King George for a permit, and any insurance would have been purchased by the East India Company, not the
In Cape Coral a bunch of people could just show up spontaneously because we have the First Amendment.
Congress shall make no law respecting an establishment of religion, or prohibiting the free exercise thereof; or abridging the freedom of speech, or of the press; or the right of the people peaceably to assemble, and to petition the Government for a redress of grievances.The First Amendment doesn't say there isn't personal responsibility, and it doesn't require an insurance policy purchased by one individual to guarantee the behavior of other individuals peaceably to assemble. Just like a riot in East Lansing after a Michigan State NCAA tournament loss, nobody has to get a permit and individuals are responsible for themselves. If a riot can just happen, so can a peaceable assembly.
We will need some securely anonymous social network, however, to keep the state from coming after individuals who merely pass on the news of such an event. I think in the next few years you will see this become mainstream by necessity, and it won't be because of municipal regulation.