I have a similar situation with a couple of twists. Mrs flymonthly and I are taking flymonthly Jr to college in a day and a half, flying xxx-DTW-PHL. xxx-DTW is on a small CRJ with no FC, DTW-PHL is on a DC9-50. We're all on one reservation since Mrs fm and Jr have no status and Jr has decided he needs every possible article of clothing he's ever owned as well as all of his electronics, functional or not, so we have 6 bags to check.

In true FT spirit, I'm trying to figure out a way to be eligible for upgrades while still getting all our bags free. With two companions, I can't request an upgrade, but if I split one off onto a separate reservation can we still check 6 bags for free if we don't get upgraded before check-in? Would it be possible to split the reservation and request upgrades for Mrs fm and myself after we've checked in the bags at xxx? We're within the FO upgrade window and the seat map (I know, not the most reliable indicator) shows that ours are the only preferred seats taken. There are two FC seats available for purchase so there's at least a chance of upgrades. Any ideas?