Do you regularly get offered the Uber Pass? I've gotten it once, and I used the hell out of it, so now I'm pretty convinced that I'll never be offered again.
I'm not the parent comment, but I used to get offered Uber pass immediately after the previous one expired. Recently they switched over to option to auto-renew rather than having to manually buy a new pass each time. I'm in Portland, OR so it may be location specific.
I have a friend who has one, she uses it quite heavily - routinely cutting around $250 out of her Uber costs. She gets a new one every week.