A major point of this article is that Uber skirts regulations by sticking to the letter of the law while violating its spirit, which a lot of people (falsely, in the author's eyes) see as Uber thinking its above the law. I was under the impression that Uber outright broke the law in many places. The author describes how things went for them in San Francisco: the laws never considered smartphone apps, so Uber was able…
In Philly, Uber asked for a license, was denied, then told its drivers they would cover the costs of any fines and they should drive anyway. Offering upfront to pay fines doesn't sound like they thought they found a loophole.
If the fines incurred are less than margins, then you have a profitable strategy.