You could check "Don't show me this tip again". That's why I don't remember it as the main problem with Clippy. I agree that it was a bad idea in the first place to interrupt a user's action. Finding the right time and manner to offer a suggestion is a hard problem even for a human being.
In my experience, Clippy was never wrong about that - precision and recall were absolutely perfect - but people do not appreciate being interrupted, particularly at the precise moment their work has begun.
The hard part of creating an assistant is not coming up with some stuff to suggest, it's coming up with a time, place, and manner to make those suggestions so that users might be open to them.
> creating an assistant out of it will someday become as easy as keeping a Juypter notebook running.
Absolutely true, but if you intend for that assistant to proactively inject itself into people's lives, get ready to be held to an unimaginably high bar of quality.