I am quite surprised by the lack of attention to the risks of paying someone directly for transportation service. The issue is not the relationship with the TNC but the fact that the vehicle and driver are completely uninsured if they drive their personal vehicle. Uber Black works with fully permitted livery providers with commercial insurance, but Uber X drivers using their personal cars are totally at risk with no coverage at all. Furthermore, if the TNC driver is at fault in the accident and ostensibly acting on behalf of the passenger, then the passenger is at risk for liablity as well. Make sure that your gypsy cab is really a cab or licensed limousine that has commercial insurance.