Supposedly ADD kids are delayed in maturity and for us, 5th grade is followed by middle school setting. Middle School throws in more chaotic factors into the mix (hormones and different threats/distractions that didn’t exist in elementary). A lot of people in my area “red shirt” or delay their boys entering kinder from the start knowing that boys are slower than girls in academic maturity and verbal skills. Those boys hit puberty earlier than the boys that don’t get red-shirted and that made my young son who was not red-shirted and with ADD feel odd and inferior. Many of his friends went to private school in middle school and high school starting (sometimes repeating a year) to get more individualized attention and the advantage of a repeated year in a different social setting. Wish I had that option. It’s an individual boy and family decision but those are some tactics I’ve seen. Yours will be unique to your situation. Good luck!