And Microsoft has now become quite infamous for forcing updates on the unwary--to the point that people now produce webcomics about it. I don't see that as an improvement.

The real problem with updates is all the crapware that companies like Samsung foist on people. It's shitty software that never works right but still gets delivered and then its brokenness is in the way of an operating system update because of how shitty it is.

No, the real problem with updates is that they don't exist.

You're not wrong, really. But what Microsoft has always done differently is control the distribution and installation of their own updates. With Android it's always been up to a combination of Google releasing the update, the manufacturer putting their touches on it and then the service provider releasing it. Of course a savvy user could get the update as soon as it is available in some cases (in other cases it'll break your phone).

I'm not advocating for really any particular way of doing it, but rather just noting how Apple definitely has the opportunity for making OS updates a smoother experience than either Microsoft or Google because of their level of control at the hardware level. Apple doesn't always get it right (see Catalina), but they could do better than they do.

Same kind of customization could be done with Windows CE and PocketPC devices, yet there were updates available.