I was that medicated ADHD kid, and I am that medicated anxiety adult. For me, medication was not a great experience. I was on ritalin, which was all that there was back in the day, and I compare it with a radio with reception problems. Ritalin turned my volume lower, making me less of a problem for teachers, but it didn't tune me to the right station. I still had the problem, but the environment didn't.
The way you handled it, with care, caution, and checking in, taking the kid in to the doctor as needed, is exactly the right approach, and I applaud you for it. The process of trial and error is one familiar to many of us who are on brain meds. It very much isn't one size fits all, and you gotta find the one that's right for the person. You are doing that.
Thank you @didic, it is great to hear the experience from your side too. I guess there are many sides to stories like these, the point of view of the child, the point of view of the child grown up into an adult, the parent and the doctor. So many things to consider! We have to have a very open mind and watch carefully I guess