That is such a great post, Terry! I've thought about that a lot as a mother of a large family, in reading many JW stories, and seeing lots of YouTubes.
As you said, being a christian, following Jesus was more than just obedience. -- I've noticed that in JW world, it seems like all the parents care about with their older kids is that they...... GO TO THE MEETINGS. Many are not even caring/trying to persuade them of the truth of it all, as long as the kids keep going to the meetings, that will keep the parents happy.
With most of the Christians i know, from various denominations, keeping the kids 'in church' is not the main goal. We desire that they come to the Faith, really and truly, in their hearts. And this cannot be coerced. Many allow and even expect times of questioning, doubting, etc. Our goal isn't to have their bodies in a pew to please us or make us look good.
My own son is almost 17 and hasn't attended church in a year. He is reading about all kinds of religions right now, and makes no claim to be a Christian. How can i deny him his own spiritual journey? Do i pray for him? You Bet! Do i try to make little points occasionally, or suggest things for him to read once in a while? yes. Do i look down on him for this? NO WAY.