I don't think that's really true in this case. In the few cities I know any details for, the Uber answer was, "we'll just do it until the city sues us". That doesn't really take any special knowledge, just preparedness with the lawyers.
> Having an effective strategy to skirt regulations probably requires just as much knowledge of the regs as a company who complies with them.
Not really. The "effective strategy to skirt regulations" seems to be "when someone makes an issue out of it, we'll burn investor money on PR and lobbying against the regulations, and on paying any penalties that get assessed for violations".
For that, you don't need much advance study of the regulations, just a deep supply of investor funds.