My older son had a lot of issues with depression and social anxiety when he was in high school. He wound up attending a charter school that is one of only a couple of public Montessori high schools in the country. It was good for him, mostly--though he carries a resentment that he didn't get as much math education as he thought he should. The setting was perfect for him, though.
Sounds like everything will work out--that sense of flexibility will be important for both of you to cultivate. "Ideal" isn't always possible, but of the "good enough" is.