Black Sheep - No. Don't do anything to trip opposer/apostate flags. Information that impresses you, might just scare her off at this point. Save that for much later.
Ask questions based on what she shows you and tells you. That way, you don't have to bring anything new to the table.
She has to realise that she is teaching you a load of crap by doing her own research to answer your questions. Don't do it for her.
Hi educatingMyself. I agree with Black Sheep. Spend time with the lady and learn from your experience without the expectation to free her mind. If JWs are not spending enough time with her, she may enjoy the experience. I am kind of curious how the changes in JW doctrine from "1914: the Generation that will not Pass" to "Overlapping Generations" would have changed the lady's retirement plans. If the Apocalypse may not happen for another 100 years, would she have done things differently?
Peace be with you and everyone, who you love,
ABibleStudent