Thank you all so much for your insights!

When I think of it, it really seem as though he doesn't understand simple tasks because he is always expecting something more complicated. I will give him instructions and say this is all it is, he will follow up with " you mean I just..", "I just have to do..". Confirming over and over that what he is supposed to do is really just what I am explaining. It is like he is always suspecting there is more to it.

Even when I ask him to go get something it might sound something like this:

Me: Could you go in your room and get ........,it is on the dresser.
DS: You mean the dresser in my room?
Me: Yes, the dresser in your room.
DS: Right by my bed?
Me: Yes, dresser by your bed.
DS: It is on top of the dresser in my room?

Like he is having to confirm things over and over to make sure he got it right.
This is a bit different than how he complicates things overwhen we do schoolwork. Almost seems as though the auditory processing is not working right.

He is also very insistent upon things being done right. One sheet of homework was counting fruits. The answer was supposed to be five, but one of the fruits was a cherry, not just one cherry but two stuck together like they are. But it is was still supposed to be counted as one. He refused to say they were only five fruits. He got very upset and kept saying there are actually 6.

On a test in school there was a question where you had a group of five books and a group of two cats. The question was what is less than 5. You were supposed to circle the group of 2 cats. Instead he draws 4 things and puts 4 as his answer.

Overall it seems a lot of the time he does not see things for what they are. He always dissect the question and completely complicates it. Does he get it right when he does it the way he figured he was supposed to? Yes, absolutely. When he complicates the question and does it, the answer always makes sense. Of course it is not the answer that was expected though.