Jonah:
You missed the Friedman solution completely. In a true free market the city would have offered X number of passes in an open auction. Instead the city acts like the worst combination of suffocating bureaucratic state and big bidness monopolist. It sets an arbitrary “price” and calls it a “market”.
Further, a true market solution would have encouraged car pooling. Yes, car pooling. When 4 co-workers combine their funds to purchase one pass for use in multiple vehicles on different days.
Even further, a true market would have a secondary level of transactions where those who own passes might trade them with other consumers for such things as bacon, Clash CDs, or even pounds.