Uber's website states that they maintain coverage on top of all drivers' insurance, not just black. I can tell you definitively that there must be some pretty good fine print on that in terms of how often they check/verify instance because of both my friend's experience and because of another friend that works as an insurance adjuster who admits to denying claims all the time from uber/lyft accidents because they weren't notified that the driver was doing commercial driving.

I guess I'm just not willing to risk either my 8 figure career or the short term possibility of 5-6 figures out of pocket when OJI is denied and then my personal insurance is denied because I already tried to OJI it. I mean risk/benefit analysis is I'm risking my career or 5-6 figures in order to do what? Make sure that we're at the gate on time so that we can push late waiting for the ramp to load the bags?

No thanks, I don't trust the company to do the right thing. Ask anybody you know if they've had a seemless OJI experience with the company. I don't know a single person who has.