I don't know from shinola about being a parent, but I do have some observations about school and success there. First off, I think 'success' is way more than grades and 'progress' and that it's relative to each individual.

I predict that smallsteps will succeed simply because she comes of good stock with parents that give a shit AND HAVE PROVED THEY GIVE A SHIT with her problems. I had enough health problems (mostly self inflicted) that I knew at a visceral level that my parents had my back. I think that's important.

I grew up mostly isolated. Nearest kid my age was 2 miles away and that was a girl. Ugggghhh. That she turned out to be a really pretty girl didn't interest me at all for years, and then it was too late :) So I don't think smallstep's relative isolation will necessarily work against her at all.

Worry and self depreciation are part of the human equation. One thing I know is that you guys have ALWAYS made the best choice based on the information at hand. That's a good trend line for anyone.