A few thoughts as a bike commuter in Manhattan who sees this first hand every day: The congestion tax can't come soon enough (and it should have no carve-outs, certainly not for people who live here). We need to get rid of lots of free on-street parking in the city and replace it with loading zones so that taxis/Ubers and trucks have free spaces on every block to conduct their business without blocking travel lanes o…
Part of the reason these companies can get away with settling is due to the large volume of tickets they receive. In the case of a fine escalating for each ticket, I would imagine that the company would then fight each ticket in court. This could easily overwhelm the courts. This seems like a fundamentally unfixable vulnerability that has been exploited by other actors (like Scientology).