Government regulation is a two edged sword. An unrelated example is the environmental regulatory agency in the USA. Before regulation, there was quite a bit of pollution. Rivers would literally catch fire, for just one example. So the EPA was formed and pollution was curbed. Now this agency, for, what seems just the sake of justification of existence, was looking to regulate cow farts.
So, the question there is, is the city trying to make money or is it the taxi industry lobbying the city to make getting a medallion so difficult to protect their business?
Regulation makes sense in that a taxi service should be appropriately insured and the vehicles well maintained and safe. Could that be said of all vehicles in the Uber service. Can one, at a glance, know if the brakes are in good order before jumping in the back seat? Is the vehicle even insured? Will you be covered if the vehicle is involved in a crash and you are injured?
On the Uber driver side, will the driver be protected against a law suit for whatever reason? (crash, person loses job because of being late because the driver got lost, etc.)
There has been much regulation that is the result of established business lobbying to protect itself from competition. As said, regulation is a two edged sword.