A FlyerTalk Posting Legend
Join Date: Sep 2009
Location: Minneapolis: DL DM charter 2.3MM
Programs: A3*Gold, SPG Plat, HyattDiamond, MarriottPP, LHW exAccess, ICI, Raffles Amb, NW PE MM, TWA Gold MM
Posts: 102,617
Why not book on the same PNR and split just before the PM upgrade window opens? That way the GM probably keeps C+/EC unless there's a late schedule that causes seats to be shuffled.
Also, AFAIK it's still an unwritten perk to be able to bring one person on a separate PNR into C+/EC with you.
You might get better advice if you tell us the route, day of week (or holiday period if applicable) and approximate time of day.