In answer to your question, yes it does matter, not so much because of the past, but for the future.
Each generation has had it’s problems; you’re right about that, but the nisyonos have changed. The ta’vah for avodah zara is gone, so that battle has changed. The challenge presented by the haskalah has all but disappeared, as well. Today’s youth are, for the most part, confronted with a different set of chalenges, not the least of which are dealing with today’s technology and the decadence it allows, the overall moral decline of society and its infiltration into our communities, and the high stress level of today’s fast paced, hectic world.
How to deal with these problems is essential to keep our children in the fold, and identifying causes for youth leaving the path of Torah is an important key.
In your role as mentor to youth at (or beyond) risk, it is indeed more important to deal with the individual. It’s also vital to deal with our still frum youths as individuals, but our society’s norms are generally dictated by what’s best in general.
It is how to structure these general norms and policies which are the subject of much discussion and debate. Don’t belittle it just because your personal tafkid is, rightfully, focused elsewhere.