re: grapple leapfrog, it links to this question: https://rpg.stackexchange.com/q/136964
Maybe the AI used the accepted answer (with 4 votes vs the next with 39) and then mangled things from there?
re: counter chaining, I think so. I spent some time watching Critical Role and iirc they liked to counterspell a counterspell.
First one is pretty easy. The player is just trying to do RAW instead of intention. Intent obviously is that while dragging every feet of actual movement costs two of your characters movement allowance, so dropping the burden doesn’t give you more movement.
Countering a counterspell feels like a waste since for one you have to have another caster with counter spell and now they are wasting their reaction plus a slot instead of just going another round. I guess there are situations where that makes sense, but somehow feels bad