> One could easily argue that the people showing an unreasonable entitlement are the ones who think they should get to use the park in the tiny sliver of time where someone else has paid the city to reserve it for an organized game.

Your argument seems to be based on the idea that people with money intrinsically have more right to something than those who do not. I understand this is the prominent view in the US but there are other ways to do it(there's a big gap between communism and ultra-capitalism). Look to the scandinavian countries for instance where they place a far great emphasis on wealth redistribution and community support through better schooling and healthcare.