My plan this time is to not check-in until I get to the airport. Last time, I checked in ~20hrs before the first flight, and I think that removed me from the waitlist, as you can only be waitlisted and not added to the day of departure upgrade list. Once you check-in, I think it removes you from the waitlist.
My thinking is, if they open seats after 24 hours and anytime up until you check-in, that I will have a better shot at getting the upgrade.
This is of course assuming it is all coded correctly in the reservation.
Hopefully this works, even though I'll be burning 60k miles, I'll give it a shot.