Master of None - I can't speak to your situation but I will tell you about a friend. Her DS had a horrible time in school. He was diagnosed with ADD, anger disorder (can't recall the name), and Asperger's and the school wanted him medicated. Finally, after 2nd grade, she pulled him out to homeschool. Everyone said he need to be in school to learn social skills, to learn how to deal w/ issues and manage his anger/anxiety. Well, you wouldn't recognize this kid just 2yrs later. You wouldn't recognize him 6months after he had been Hsing. ALL adults in his life noticed the change. He was more confident. He looked people in the eye. He initiated conversations. He didn't have the huge, out of control anger explosions. His attention was just fine. Now, you'd be hard pressed to diagnose him w/ any disorder. It was simply a toxic environment for him. This kid is DYS-level (never applied though) and just wanted getting his academic, emotional or social needs met. I think he needed to be a in a safe, controlled environment to learn social skills etc.

But if he's not for HSing and it would entail a huge life change for you, HSing might not be the best choice. But, also, nothings set in stone. If you try HSing for a year and it doesn't work out, could he go back to his middle school? Could you return to your job?