Well - you can see a white dab of paint on the "outside" side of the connector on the NIC in my photo. The AAUI daughterboard has one as well. This matches up with the square screened around the one pin on the solder side of the board.
The blue connector on the ribbon has the molded arrow which points to the brown wire which I think we all believe is pin 1.
I'm pretty confident I know how things line up at this point. Thanks everyone for their help!