Basically, this. My first tech job was IT support at the time and ordinary people using their computers for actual work liked them too. I remember the dog/puppy being particular popular. At worst the assistants were seen as charmingly naff, not actively hostile. They were simple for power users to disable and this weird retroactive hatred for them feels more like some kind of nerd bitterness over the fact that normies ever started using computers in the first place. There was plenty of reason to be critical of Microsoft in those days that wasn't their office assistant.

> I liked Clippit

Yes! It was called Clippit! Why is everybody calling it Clippy these days?

I feel like it's a Mandela Effect [1].

[1] https://en.wikipedia.org/wiki/False_memory#Mandela_effect