I found this absolutely fascinating. Auld Soul, your use of the JW doctrines' own internal *simulation* of logic was very well-done. I suspect that you might have started her thinking, against her will--but as you noted, since you were entangled in her "deal-breaker" question, she'll move you from the "he made an interesting point" list to the "that guy just doesn't get it" list.
I think Gary's comment about needing to teach JWs their own doctrine before you can talk to them was pretty spot-on. That's what makes it so frustrating.
I don't have nearly the academic training and scholarship that some on this board do, but have taken enough religious studies course to acquire a minor for my B.A. in English (which means I've got more formal religious education than anybody on the GB, doesn't it?). It's been enough education to leave me amazed at the way JWs insist they have "accurate Bible knowledge" when all they've really got are a handful of proof-texts provided to answer specific questions. Ask them anything else, and they're befuddled.
What's even more sad is that, because JWs focus on one doctrinal question at a time, they can't see the inconsistencies in the whole of their doctrine. By getting lost in minutiae and pondering how many angels can dance on the head of a pin, they manage to miss the fact that they deny Jesus. Talk about the beam in the eye!