Join Date: Nov 2000
Location: Nashville -Past DL Plat, FO, WN-CP, various hotel programs
Programs: DL-MM, AA, SW w/companion,HiltonDiamond, Hyatt PLat, IHF Plat, Miles and Points Seeker
Posts: 11,405
Yes... does not matter which one is the "paid" vs "free" flight.
As to both boarding after the A group together, do not know. In practice, as long as you have booked your flight at least 36 hours in advance, you both should be in the A group anyways.