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.
This is one of my "worry" areas, because she is good at the task stuff and loves it, but it really doesn't account for much in the rest of life - so she will have to find some balance.
What I find is, the kids who live somewhat isolated lives, often end up more thoughtful and self-reliant and directed.
We do have a trend line of some sort :)