I think it is a typical Disney not-policy situation, where it depends on the cast members you're dealing with. I stayed at POFQ for a conference that was being held offsite and Ubered back and forth (because seriously, how could I go to Orlando and stay at a Marriott?!?
). Most of the time drivers had no problem getting in to the resort, but there was one occasion (out of 5 or 6 pick-ups) where a security guard didn't want to allow the driver past the gate. From talking to a different driver later in the week, I gather it is partly a matter of how the driver handles it - saying they're from Uber doesn't always go over well with security, but saying they're meeting a friend who is staying at the resort works just fine - but also variable depending on who is manning the gate at any given time. And it is possible that some drivers have a standard pick-up point for the resort, rather than trying to coordinate meeting in the villages.