After some back and forth consisting of me walking her through the process we did get our PR-1 status, though for some reason AJK was listed as #1 despite the fact that he doesn’t have United status and I was listed as #2 with my 1K status. Go figure.
Well, since I know just a little bit about the UA internal system I will explain.
The correct code for PR-1 status is waitlisting the PNR using a SSR called
PA (It goes down to PB/PC/PD). PA is used for GS members, now since you (and AJK) don't belong to be waitlisted as a PA, ONLY GS members belong in PA, the system does not prioritize the customer based on status. Since PA accommodates only one status, GS. While the matter that does factor is fare class and time of request, since you were both holding the same fare class the next factor was time of request. And I would guess that the agent requested AJKs upgrade first, that is why he was #1. If you think its worth adding this to the comments on the MS, LMK