Re: CTL,
I can’t fully discuss what exactly his upbringing was, I was not there. I do agree that pre-war and later American Jewish life was in bad state. I heard from R Nosson Sherman that his father would tell his elderly members of the shiur to come even during bad weather – “because who knows whether there will be a shiur after you”. Not clear where things were better. Chofetz Chaim letters c. 1920 from Poland talk about not sending kids to anti-religious schools, closer to 1930 he talks more and more about at least keeping Shabbos, Nida, having at least one kosher cheder per town, and even a suggestion for T’Ch to travel to different towns because maybe people who did not listen to one T’Ch would listen to another one.
Did things improve by now? On one hand yes, we have big observant communities. On the other hand, “the rest” of the Jews look completely lost, as Chofetz Chaim was warning about. In 1960-90s there were a significant number of baalei teshuva, which I think is not happening to the same degree now.