The talent book idea sounds like a coping mechanism that a smart kid would come up with. The chink in the armor of course is that these delays don't just get in the way of things he doesn't care about doing but touch up against things he may really value - math, music, being with other people and of course feeling well. I think it is great if he can embrace his strengths, but I would look a bit past the surface comments there. Kids often say they are too cool for something that scares them or that they have to work at - it doesn't mean there isn't hurt underneath.
I wasn't clear from your post. Is your belief that he sees you are pessimistic but his whole view of that is that it is funny? Do you think on any level he hears your worries as a lack of trust and confidence in his abilities? I'll be direct - it is hard for me to really believe any kid would not pick up on this and feel bad about it. At the very core of it - helicopter parenting says to the kid that you don't believe in them or trust them.
