I have both Windows and Linux desktops, and both annoy me tremendously during updates. On Windows its a new feature that I have to 'click to disable' and on Linux is a new feature that completely screws up my settings and I have to click to go back to the way it was, or construct my settings using the new paradigm.
Both of these annoyances are driven by software change. As the software changes, it changes the environment in which it runs, and symbiotically a bunch of other things change. Why do these things change?
Basically capital. In the free software world it is intellectual capital. Most people who want to contribute to open source, want to do so by "creating a new feature" or "improving and existing feature to be better". Few people want to contribute by "fixing compatibility bugs" or "fixing configuration confusion." They have intellectual capital to spend and they want to spend it on change, not on status quo. In the commercial software world it is worse, they are constantly paying their programming team, every day, every week, 11 paid holidays a year. They can only do that if they have revenue. And they get revenue by selling change not by polishing the status quo. So they change things and they get 'creative' about ways to get revenue.
The ugly truth is that the software business could in fact be "done" for a lot of things. You could just declare the kernel "done" and only allow bug fixes or new processor support. You can declare AutoCAD done and only fix bugs or add GPU support. You can declare graphics Done and simply build GPUs that do what the graphics library need, perhaps a bit faster.
The world changed in a fundamental way when computers got to be 'fast enough' for the imagination of people who wanted to use them. Upgrade cycles started lagging and now it is not uncommon for someone to have a computer for five years before an upgrade. Microsoft needs to make enough money on the OS they sold you once ever 5 years to pay for a crap ton of developers. The math doesn't work, so they are being 'creative' about other ways to make money on those users. Linux/FOSS needs new developers to survive but those developers mostly want to work on 'features' not bugs. So Linux systems suffer arbitrary feature churn.
I think the author's peeve is a symptom not the problem. The problem is that the money is leaving the software space and without it commercial software is not viable.