The Medium UI is a pain, agreed. I use multiple tabs or windows to keep it all straight.
I also agree that the soccer analogy didn't work as well as I had envisioned. Should have done something else. It was worth a try, I suppose, but I ran out of time to edit it to something else.
Finally, I still don't think you've adequately addressed the chilling effect of the threat of lawsuits. If the "third option" includes repealing some of the anti-CRT legislation, then say so. That would remove any chilling effect of lawsuits.
Otherwise, even if you envision a third option, the point still stands that the laws may have a chilling effect. Your sympathy doesn't fix the problem. You might solve the tradeoff a different way than Tim would (keep laws, accept chill), but it doesn't mean Tim is wrong on this.
In other places, where Tim assumes that it could only work one way, and "how about no political indoctrination at all" is an unrecognized third option, it can be a good answer.