[OkayPhysicist]

Your first two examples were predicated on the evasion of laws, and the taxi example literally states what law it was evading.

[latchkey]

Tax medallion's were created by the Taxi industry to regulate "cabs" and keep the grift going.

Using your own car as a way to give people rides, and get paid for it, fell into a grey zone because nobody had actually thought to do that before.

Let's also not forget that this is a global business with different "laws" all over the place.