Aries, first of all, Mazel Tov on what must surely be a very proud accomplishment both for you and for the young man. May he bo zocheh to build a B”NB with his kallah.
I agree with virtually everything you posted (Philosopher is a she, btw), and I believe that love is mekareiv and harsh words and a “my way or the highway” attitude will have the opposite effect on someone already disenfranchised. The words that resonated the strongest with me, were when you wrote about the nachas of being off a suicide watch. Unfortunately, I am acquainted with two families who lost children to drugs (we want to believe the overdoses were accidental), but the pain of these very nice members of the community is still palpable after many years, nebbich.
Whether by deliberate suicide or accidental improper combinations of drugs and alcohol, the unfathomable pain for the parents of these kids can never go away. I applaud the rebbies, community members, professional therapists, etc. who look at these types of yiddishe neshamas as “lost” but not irretrievably so, and try to help them, not condemn them.