So two more calls to AS and one to my TA and it is resolved, and I am waitlisted for u/g

Turns out it was indeed an error with the TA's system, the 016 flight number was only for the UA segment and they had failed to ticket the AS segment. They took care of that and the itin moved over to "Purchased" on AS.com and a "Request upgrade link appeared"... However the upgrade request failed several times -- but a final call back to AS and the agent was able to request it, and the request now appears online.

Thanks for all the advice