It is possible for a very small group to cooperate and take advantage of privileged information. On Manhattan's Upper East Side a pediatrician and food vendor have developed their own club that monopolizes a street space. Here is a Gothanist story about them. From the story:
An Upper East Side pediatrician and a food-cart vendor have been saving a parking spot for one another on East 96th Street for two years, surprising everyone who believes this city is the glorified embodiment of unchecked egotism. The Post reports that when Dr. Doug Waite pulls his Volvo out of the spot at 8 a.m., Sait Kumtas pulls his van in. At 6 p.m., Dr. Waite honks three times and Kumtas relinquishes the spot.The vendor's van is even in the Google Maps street view photo.
Instead of throwing vast sums of money at the problem of finding a spot, the men agreed to "cooperate" (a term that originated in the Midwest and means "share like suckers") after they happened to make the swap by chance. “He was my customer,” Kumtas says. “I knew him, and we would say hello."
Everything is fine so long as they remember to give each other a heads up when they're going on vacation. “Once, we were up in Maine to visit my son in school and I got a call on my cellphone from Sait, wondering where I was,” Dr. Waite says. And Kumtas didn't even slash his tires or punch him in the face!
So these two realized that cooperation was mutually beneficial. How large can their parking club get before cooperation breaks down? Probably not very large, but what these two are doing with one space on the Upper East Side is essentially what all the smart phones parking apps are trying to do for all parking spaces.