I have to jump in here, to add some information about what generally starts these disputes between the pointy head government people and the homer owners.
What more times is the cause is neighbors complaints about traffic in the neighborhood, from the looks of the size of the parking lot there are expecting more than three or four cars at a time. I know in our city (small) the car cruise night downtown is a pain for those that live closer to it. I'm 8 city blocks from the area and you can hear the burnouts and noise from the engines being revved and no where to go.
But what is worse is the fireworks nights as the people park everywhere across your driveway entrance, and sidewalks. Then the fun starts when its over and the drunks start throwing the bottles and breaking them. It is a real pain for the people that live near the world famous Woodward Dream Cruise route for the week leading up to it.
So since it is a big money maker for the city (permits) sidewalk sellers, food trailers, etc You know its to keep the public safe.
Along with local businesses that are raking in the money, any problems fall on deaf ears as the standard answer is we will address it at next years planning meeting. Which of course is always short on time.
And yes the insurance for the private party use let alone the public liability would shut them down in an eye blink. Currently there is a guy that is suing Hooters because they wouldn't hire him as a Host to serve beer as they only employ women
http://www.hooters.com/ the start of it was the Want to be a Hooters girl on their site.
So inviting the public onto your property even for a trunk/jumble/garage sale can be wrought with danger.
And he probably started out with the wrong attitude towards the city official(code violation enforcement officer) as they are called. Then it will go down hill from there. A money maker for the cities checking for permits, fines and then the permits. And don't forget he would have to bring all his property up to code for the disabled public including the proper toilet facilities.(Federal ADA laws)
Its to bad that he will probably lose as you can't generally fight city hall and win. Seems the only one that will win is the lawyers that will be ligating the case for years. I hope they can work it out for the positive. and his continued operation of his RR.