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To me, these seem like positive indications. They suggest that he has progressed well beyond reading as a mechanical exercise of putting together letters to make words and words to make sentences. Instead, he is making contextual “guesses” about what is coming next based on the thoughts and concepts. But at the same time, it seems to really slow him down. He spends a lot of time re-reading phrases and sentences. He also seems to tire easily. After 15-20 minutes, he gets sloppier and slower. As a result, I'm not really sure what I can (or should) do.

From the symptoms you describe, I would have to agree with this paragraph. I interpret what you have described as indicating that he is quickly establishing a gestalt WRT what he is reading, and he is then devoting no more mental capacity to the mechanics. He is responding to you out of the gestalt, which leads sometimes to peculiar results.

I would interpret it as a combination of immaturity and boredom. You might try some more challenging material, specifically on a subject he is interested in.

I don't think I'd even worry about the possibility of overwhelming him. If he is interested in the subject, being overwhelmed might just cause him to focus more.
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