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at home he pays attention but just seem to overthink, and complicate things. He will ask lots of questions before answering, trying to cover every possible detail, "But this is...", "That makes no sense...", "You mean this or this...". I try to tell him to just answer the question, but there is usually not just a simple answer for him. There are always a bunch of different angles.

This sounds a little bit like anxiety to me. I recognize some of what you are talking about in my DD, who has anxiety. Also, it does sound a little bit ASD-ish...the behavior is also not unlike my DD who is kind of gray area for ASD.

At the same time, my other child is really just NOT ASD BUT is HG. He will overthink things because he is bored/trying to make it more interesting. It can be hard to tease apart, but having the two children, I now kind of see one as one thing and the other as the other, if that makes sense. Yet they are similar!!