RayofFlight, I agree with you and I have said this to others as things to consider when telling a jw friend or family member some seemingly lightbulb moment info.
"It would appear any help we offer would be based on their level of receptivity.
And the information would need to be tailored to the individual, so building a rapport would be necessary.
And I've heard it stated somewhere before that nobody likes a rude awakening, rather, we should be ready with a hot cuppa when we hear them stir from their slumber."
I remind them that they did not come to see the real truth behind the teachings of the WTS all at once. That should make us see that they probably will not either. To keep the door open, ask thought making questions and leave it there and let them think about it. I try to let them know I wonder how they would answer my sincere question.
My comment was only what I would do or have done on JWN and in my previous jw life. I hope it did not seem that I was saying others should do what I have done and said. I have over 3 or more years posting on JWN, convinced some JWN readers that are still in to finally make the leap; how do I know, they send pms to me letting me know how I helped them and that I should not give up because not all who make the leap, necessarily let me know that I helped.
I tell readers and posters that only they really know this person, their personality, past, and current lives. To take it slowly, not bury them with several points. Just one topic you know might get them to think outside the box. But leave it if they don't respond to it. I usually let such people come to me rather than me to them, staying friendly, caring, and loving. Not to attack the WTS, but rather to concentrate on what the bible says but not make the conclusion for them. In my case, I did not realize how deep the teachings were in every congregation. How people with sincere doubts were not allowed to express them respectfully, were told that eventually God would clear up their confusion. After 25 years, 8 congregations, 3 countries, I realized how pervasive jws were told to basically shut up and wait on God.