Your romanticizing of "the government only allows so many yellow cabs so the artificial scarcity leads to medallion costs spiraling ever upward" is fucking bizarre.
Before the 'ride share' apps, taxi cab drivers was a highly paid position.
That's horseshit. People who owned the medallions made money leasing them to people who would work their fingers to the bone to cover the costs of their leases and support their families. You also ignore that most taxi companies weren't running medallion taxies with the right to pick up a hail, but rather "private cars" that had to be dispatched to a pickup location by law. More on those later.
The badge that let you drive a cab in NYC sold for $1 million dollars. You would drive it yourself 1/3 the day, then hand the cab off to employees. You would make enough in 10 years to buy another badge, then in 5 years get a third, etc etc. Your employees would save up for 15 years to buy their first badge and start the process over again.
Ignoring that "employee driving a taxi has a million dollars in savings after 15 years" would be the exception and not the rule, that sounds suspiciously like a pyramid scheme.
The apps charge you money which you think goes to the driver. Nope, most of it goes to the company. They pay the driver barely enough for the gasoline, car payment, and insurance. They expect the driver to make a profit from their 'tip', treating them as a waiter, rather than the owner of the equipment that makes the business possible.
Remember those "private car" services I mentioned above? Other than them typically owning the vehicles rather than the drivers, this is exactly how they operated. My mother drove for one in the mid 80s after her brokerage went bankrupt and she was looking for a new firm. My aunt was a dispatcher for another one for years. The drivers got shit pay and no benefits.
Despite your claims, the "ride sharing" (I think we can at least agree that part is total bullshit) companies have not meaningfully enshitified taxi services. They were always shitty.