To follow up on all of this, in case anyone is interested, through a combination of checking the GDS, messaging Delta Assist when I saw inventory, and taking what I could get at the gate for the rest, out of 10 segments this week, I will have flown one in coach and the rest in Delta One. I was able to confirm a couple of days early an upper deck seat NRT-DTW, which I leave on in a little over an hour.
I was never below #1 on the upgrade list for UGs that went to the gate, which is a good thing, because a couple of them only had one J seat available by the time upgrades were cleared.
Ironically, the only leg that I flew in coach was a 7 am JFK-SEA before connecting on to NRT. I would bet that I was either a victim of FCM on that one or that there were IRROPS the day before that filled up the first class cabin on that flight. I was number one on the waitlist for 0 seats.
Anyway, I appreciate all of the input. My comment on any survey that I get will be that I hope that DL will provide the same training for Diamond phone agents that they provide for the @DeltaAssist twitter team. HUACA is a PITA, but I always got great answers in short order from the twitter team.