I think the trick on using upgrades is this:
1. Avoid EWR and IAH. Hub city personnel know the rules better. Try to upgrade from your Origin on any segment that connects in EWR or IAH.
2. When checking in just ask if they have any F/C seats available for upgrades. Don't tell them you're using Prestige Pack upgrades. I said I was using upgrade certificates.
My wife an I went DFW-IAH-BOS this past Fri and sure enough the DFW agent booked both of us in First on thi IAH-BOS segment without looking at the certs.
Yesterday on the return BOS-EWR-DFW the BOS agent did them same on the EWR-DFW segments.
So with 6 upgrade certificates in my Prestige pack I'm batting 4 for 4.