This thread is great and I find chizuk in it. If Yanky's story is so common then it's not that hard to do a better job. You don't need to be a perfect parent, just don't be Heshy.
On the Chareidi Classic post, I don't think it's so simple. Every generation is different with different nisyonos. Although going back to a simpler time is appealing, it's not realistic. We're more affluent today, more integrated than we were a generation ago, so we've changed, and the world has changed even more. The level of connectivity and access to negative influences is not only greater than it was, it's IMPOSSIBLE to restrict or control completely. For these reasons, chinuch today CANNOT be what it was a generation ago. We need to build our children from the inside out. They can't be taught to hate or reject the outside world, they have to learn to love and revere the world of Kedusha. The older generation used simple messages but faced less resistance. We have to light the fire of Ahavas Hashem in our children (Dov knows how to do that...enter stage right).