Most importantly, Clippy happened before computers were permanently online. For it to harvest any data, I guess you'd need to mail in a floppy disk.

I doubt that. Privacy was eroded slowly through successive micro-violations.I remember when it was a big deal that gmail inspected your email contents, "but don't worry, no humans actually read it, we just mine the data to suggest better ads, but hey you get 'unlimited' storage when hotmail limits you to 4mb, so there's that!"