if she asks me about my experience as a JW
To me it sounds like she might not, if it were me I'd initiate the conversation and ask what she thought and wait to see her reation. If she then says she is thinking of going back, I would say "before you do, why not check out both sides of the story, you might find a few facts you didn't know about"
As to helping out, on this occassion it would be a conscious decision (how institutionalised does that sound!), but I would weigh up amount needed/why needed/who is it for etc.. Nothing wrong in being charitable, but another being taken for a mug