Avram:
You wrote: “And whoosh – out the escape hatch you go. Boundaries are good, but only if you “teach” them beforehand, and it’s almost impossible to teach them all beforehand. And now they’ll just be viewed as punitive. So…”
Boundaries can be taught to anyone. But the teaching methods must be a fit for the child. Shlomo Hamelech told us that. Parents were not given an instruction manual upon birth of the child, and must try to accommodate the best they can. It works most of the time, but sometimes do not. I have watched parents who recognized that a child responded to teaching in different ways, and have taken steps to accommodate. While there are more options today than there were a half century ago, we are more apt to push our kids into the molds of the yeshivos, with far less accommodation than ever. And we have the fruit of such labor. More OTD kids than any time in our recorded history.
If our teaching of boundaries failed, instituting them after the kid is already into the phase of acting out will certainly fail. You may be fortunate that no acts of chilul Shabbos occur under your roof, but you may not know the whereabouts of your child. This is not a simple dilemma, and there is no “one size fits all” answer. Presenting boundaries to the OTD child might sound “right” but it is ineffective. Our real questions should be, “What will work?” “How much compromise is appropriate?” “Is this kid ready for kiruv and embrace?” “What are the child’s needs at this time?”