Originally Posted by
WWads
Only one companion would be eligible for the upgrade, and your +1 would drag you down the list. The earliest that you could clear is T-24, and you would clear below FOs for upgrades at-gate.
You can book separate PNRs, and then link them together to get the free bags. Just make sure that the agent doesn't request a companion upgrade for whomever your +1 would be.
Yes, the reimbursement would cover the entrance fee, although I'm pretty sure that you have to pay for club access using your Delta card to get the $29 discount (not totally sure though).
Technically, linking PNRs does nothing but add a note that the pax in the different PNRs are somehow connected. If you do this and your friends go try to check in online, they will still be asked to pay for their bags. Their BPs will still read zone 1 or 2 and not SKY.
If you are not on a single PNR, you are fully at the mercy of a kind check-in agent to waive the bag fees for your companions. It often depends on airport - I often can get agents to do this at ATL, but have never had success at IAD.
The Amex Plat fee reimbursement ($200, not $250 IIRC) does cover guest entry fees and the $29 per guest per entrance fee is a feature of the unbranded plat as well as all the DL Amexes.