I figured this would be the easiest way to reply to all...
I have taken the insurance, and liability issues into account.
First off, I'm not in New York City, or State.
The Corolla has a policy with Progressive, completely separate from my other two cars (actually, a different company all together).
My friend is on my policy (this took a bit of work, but it can be done).
The car is insured for personal driving, as well as ride-share (including the time when waiting for a call, en-route to the call, while driving, and upon completion), as well as specified that there will only be certain times the car is used for such purposes.
I've checked, and double-checked, to ensure that I'm adequately covered (above state mandated limits), as there are many things that are questionable about the Uber policy, I'm not trying to skirt any regulations, or pull one over on my insurance company.
I appreciate the feedback though, many of these points were brought up when I spoke to a different friend who happens to be an attorney.
I've also made periodic checks with, and calls to, my insurance company to ensure that the multiple sources I've spoken to at Progressive have provided all the same information, as well as having it documented.