While I side completely with the town in implementing a drone ban based on expectation of privacy & trespassing issues, we all know, (or should know), that so far, the FAA regulates "airspace". I believe that the very definition of airspace is going to be revisited in the courts soon. There always has, and continues to be, an expectation of privacy and protection from trespassers on private property. If you climbed over your neighbor's fence, into their yard, there would be no question that you were trespassing and you could/would be prosecuted. The appearance of drones has muddied these formally crystal clear waters.
I believe Mr. Singer will prevail, because the court will have to rule using the current law, meaning the FAA controls airspace and no other legal entity has jurisdiction, even though their actions were well meaning.
Having said that, what I find curious is Mr. Singer "representing himself", in the legal action. That, to me, appears to be a overconfidence, bordering on arrogance.
It was after all, Abraham Lincoln who said, "He who represents himself has a fool for a client".