Appreciate the insight. Just wish AA was a little more customer savvy and upfront. None of this mysterious "maybe, maybe not."
Well how are they supposed to know?
Your position on the wait list can change significantly so what's the point in telling somebody who's just going to get annoyed when they get pushed down (see any number of threads on the standby upgrade list). What exactly are you looking for AA to be more "customer savvy" about? This is a dynamic process they don't want to give seats for upgrades if they can sell them. Most business class seats (particularly the most profitable ones) are sold in the ~1-3 weeks before departure. That's why it's filling up. Yeah, they're maybe more cautious/stingy about releasing seats earlier, but if there are any seats left before departure, then they'll clear the upgrades. And surely you can appreciate that at that time the higher status customers on the list should get first dibs?
It's been said before, but if you really want the more comfortable seat, then find a flight where you can confirm it (they do exist), pay for the seat outright (AA Vacations offers *very* good prices on air & hotel/car combos), pay for Premium Economy on BA or whoever, or redeem AAnytime miles. No shortage of ways to get a better seat!