Joseph:
It is sad, but many of the life questions that can be brought to a Rov involve areas in which the Rov himself either struggles or has zero experience. You delineated chinuch. This is a sore spot. While there are rabbonim who are quite wise and astute, aside from their vast book knowledge, many are simply not equipped. If one surveys the oilem of kids that are OTD, there is a surprising number who come from homes of rabbonim and roshei yeshivos. I am not pointing a finger at them for doing anything wrong. They are just not immune from these issues. And if they could not prevent such things from happening to their own, what precisely is their expertise to share with others?
One of my pet peeves with chinuch is that it takes training and experience to be prepared for the applied chinuch, involving creating curriculum, classroom management, teaching strategies, establishing the proper relationship with talmidim as per the guidance of Chazal, etc. This background needs to be a universal mandate, and it is not. There are more such training programs than before, and we still view the rebbeim and teachers with such training to be a small percentage of the population of mechanchim(os).
So if those who actually work in chinuch every day are lacking the expertise and training to do their job, what should make me believe the Rov down the block has the answers?
It is easier than you think to pose shailos to your LOR that fall way outside the domain of his expertise. This is not a condemnation of rabbonim. They may have other redeeming qualities. And the difficult shailoh will probably result in a referral to someone with a greater expertise in the subject.