One more thought. "Not overly concerned with labels" strikes me as a little odd. I don't think labels define the child, but they sure do help both in getting the correct supports and services and in determining what and how to medicate. The therapeutic strategy would be quite different if it were a mood disorder vs. Asperger's vs. OCD. This is, to my mind, worth sorting out.
My instinct would be to get to a neuropsych and do a proper workup, because you'll be a better advocate for him if you know what he's dealing with.
This, this, a thousand times this!!!!
