It would be the insurance companies and their lawyers battling this out, not Uber. I think the difficult part of it would be for people who don't carry their own liability insurance. Normally if you are hit by someone else, you tell your carrier and they (or their lawyers) work it out with the other side's insurance company. But if you have no such insurance (not uncommon in a place like SF, where many people do not own cars), you have to try to work it out on your own. If you are a pedestrian who is hit by someone driving around waiting for a fare, you would likely submit to the driver's personal insurance carrier, but they may deny because the driver was operating as a commercial driver, which is likely outside the scope of personal insurance. Uber's secondary insurance is unlikely to cover all of the injuries given the low limits, leaving the injured party to sort out how to recover from two insurance companies and an individual, all of whom are likely to point at each other for liability. That's not easy, and would almost certainly require a lawyer.