Given my eUp situation this year, I feel like I should just throw my entire set of planned flights into a wiki

Does anyone actually have experience with paying add-ons when requesting a day of departure upgrade?

I once added a friend to the list for YYZ-SFO. He was on a standard fare. I made it explicitly clear, in writing, to the concierge, that I wanted him on the PY list. They put him on the J list. Luckily he only cleared into PY, but I've seen AC come after the sponsor after the fact for failing to pay an add-on. This can also happen if the credit card is declined. So there is a bit of risk here.

Due to things like this, my personal rule for any offers I make would be that your fare must require no add-on when the upgrade is requested by a SE.

Anyway, back to my first statement... would a wiki be useful? I might know I'm 100% taking a flight in November, but if I post it here now, it'll get buried. Whereas a wiki can be nice and chronological.