So, I got my callback from customer service today. They stated that the spend waiver not updating is an "ongoing IT issue" that they still have not been able to resolve, nor do they have a timetable on when it will be fixed. She did state that if it was close to the date of my flight and the issue was not resolved, I could call and they could manually upgrade me if I'm eligible and would have cleared otherwise. A little dubious about that, but hopeful it all works out.