I know what challenges him... not acting out when he is (oooh, here comes the word) bored. :-) Oh, and "putting up with his younger sibling."

Unfortunately, that's not a good answer for school, it seems.

Seriously, though, where he's struggled is in cases where he gets something "cold," without any explanation (ex. an enrichment worksheet on a topic they've not covered in class and which he's not seen before).

Perfectionism already runs in the family, although I'd not really heard the term much until a few years ago. So I am concerned there.