I agree with asking what he wants and what he thinks will work for him. We had the same situation as you with one of our sons. He'd been depressed about school since about 4th grade, but the elementary school made some amazing accommodations for him. But middle school wouldn't do anything, even though he had the school's highest MAP tests ever. We met with the administration and they tried to differentiate, but this was a very successful charter school and they had their ways that worked, and wanted him to adjust instead of the other way around.
I finally pulled him out at xmas break of that year and homeschooled. I set up some teacher/tutors, plus some good online classes. He did an entire year of 7th grade science in about 3 weeks. He had been yearning to just go at his own pace for so long!
In the meantime, I looked around for schools that would work for him. We wanted him at a b & m school by 8th grade so he'd have a year of practice before high school. I found a great school, he skipped a grade (he had been approved, but we didn't skip him earlier) and he entered 8th the next year. He was anxious to go back to school because he was lonely. He didn't find best friends that year, but now in 9th (same school) he has a big group of friends.
I didn't realize until I pulled my son out of school how depressed he was about the b & m school. As soon as we told him he was going to homeschool, our happy, funny boy came back. We're so glad we were able to make that choice for him. Hope you have similar success.
