It would be really easy to make such a thing as awful as Microsoft Office's Clippy ("It looks like you're writing a letter..."), and really hard to make it genu

It would be really easy to make such a thing as awful as Microsoft Office's Clippy ("It looks like you're writing a letter..."), and really hard to make it genuinely useful. I can imagine it being mostly annoying or unhelpful enough to be left turned off. The monitoring and surveillance could in principle be avoided by running the whole thing offline on the user's hardware.