I FINALLY negotiated my way through annual pass purchases.
I purchased 4 passes, 1 with photopass digital download which was displayed at the bottom of the ticket assignment list. Of course I assigned myself to the annual pass with the photopass first. I was presented with my only clue that the process would get stuck -- address the same as the first guest. Hmm, I had not yet assigned a first guest. When I assigned the first annual pass in the list, it did not ask for any address information. After filling in the rest of the form and click submit, Woody just stood around doing nothing. I repeated these steps 3 times expecting it to work (because I am insane).
Finally, FINALLY, I assigned the tickets in order and was prompted for age and address for each assignment. I completed the form, hit submit, and got order confirmation.
This is my lot in life. To be a warning for others.