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Arso,
“ the way to keep the kid aligned is to say something like, “It’s great that that woman does so much chesed, but unfortunately it’s really terrible that she is not tzniusdik. What a pity. Her chesed would be worth so much more.”
Why do you think emphasizing the negative is better and produces better results? To me that will result in seeing everyone as less than (while conveniently forgetting that I also have work to do.)
There are two parts to the person: your approach is to want everyone to see the yetzer hard in them, while we don’t excuse the yetzer hara (it’s true) but choose to pick up the Neshama in the person and be inspired.
There are many many children who have grown up into wonderful Chassidishe adults with this chinuch. Yes it’sa fine line. Everything in chinuch is a fine line.
Chabad is far from collapsing. We have only expanded both as Anash and as shluchim, especially post Gimmel Tammuz.