"Free market is not an answer to everything."

The problem here is one of rationing. There are a limited number of spots; who gets them?

In the current situation, the spaces are free/subsidized, but you pay instead by driving in circles. That's a big waste of time and adds to traffic congestion. Maybe that's more "fair" in some sense, but that doesn't make it good.

The app in question does either nothing or very little to help ration. It allows people who really need to park, and have the money to pay for it, to be more certain that they will get a space, which I guess is something. But it creates so many bad incentives that it's making the problem worse, not better.

The city is in a better position to create market incentives, because they can charge for the entire duration that you're in the space, not just the moment you happen to park. That means people would have no reason to camp out in a space waiting for the price to go up, which means more spaces will be available for useful purposes. It saves time and congestion, but perhaps loses out on some definitions of "fairness".

Any other ideas?