Has he ever been evaluated for autism (and many things now fall under Autism Spectrum Disorder, like what used to be called Aspberger’s, etc)? Several aspects of your son’s story remind me of a kid I know. In elementary school he had friends and was active in classes, and adults and older family members found him really funny, but the kid did experience anxiety issues. The kid saw a social worker but some of the issues just didn’t go away plus there were some other signs that concerned the family, so they got a neuropsych eval. Even though the social worker didn’t think it was ASD, that’s what came out of the eval, surprising the social worker and some of the teachers at school. But the people on the school’s evaluation team said it was not uncommon and that his differences would probably start to become clearer to others in middle school and subsequently.
So I definitely would have a well-trained audiologist check out your son, but just wanted to mention ASD in case it rang some bells.