I read it as "macOS is so full of issues that there's no way the CEO uses computers at all or he would have done something about it"

I would agree with this.

Jobs blasted folks for bad experiences, whereas I get tripped up by updates making me run through the OOBE, that doesn't contain anything, because its already set up.

The last update ran through the "connect to WiFi" process, and failed because it was already set up and connected to WiFi, but blocked everything until I managed to get through the pointless Next Next Next process. It felt like Windows in 2000.