Ok, so here's how our situation went down...we were flying PDX/DFW/MCO and back for a vacation - outbound on Sunday at 12:25 pm, return on Saturday 8:25 a.m. We ONLY requested the PDX/DFW segments because I think it's a waste to upgrade on the shorter flights (I think it's sort of a waste to upgrade on the PDX/DFW segments, too, but when you live near PDX you have no opportunities for better flights).
We left our home the day before so had no access to a computer, checked in for our flight at the airport and we were NOT upgraded. We did have the exit row, so it was fine.
On the way home, at 8:25 am MCO/DFW still did NOT know if our DFW/PDX had cleared, but when we got to DFW it had. Very nice FA's, food pretty bad. Choices were a cold salad with BBQ chicken, but we both wanted something hot so got the Philly Cheesesteak Calzone...I don't know if they cooked it wrong, but it was a big soggy blob of dough, I just ate out the insdie. Cookies were not chocolate chip, but rather a coconut toffee but I don't like coconut

but ate one anyway for the team
We became Lifetime Gold just a year ago, so out of our 3 attempts to upgrade so far 2 have been successful - I think that's pretty good. We actually live in Eugene so mostly flying AS out of there, so only can even attempt on our PDX flights (We go to PDX a lot for our free AA tickets, or if the fare is substantially less than from EUG to make it worthwhile).
But the most fortuitous thing was that had the first one cleared (outbound), we would have had to buy 2 stickers, but since THAT flight put my husband over his next 10,000 mile threshold, in a few days the miles posted so the one we did upgrade on we had enough stickers.
Anyway, that's my story