Four opinions, going off of this article and partly in response to Gruber's[0]: 1. There was a functional reason that CDs and floppies went out of style: low capacity and the Internet. What’s the functional reason to get rid of analog headphones? It’s not quality – analog headphones have excellent sound quality, and 99% of people won’t be able to tell the difference with ‘digital’ sound, right? 2. So what happens if…
> Maybe now is the wrong time, and Apple is making a mistake. I don’t know.
You might be responding to the Gruber in your head rather than the one who wrote that post.
He's not extolling the virtues of Apple's decision, saying it was the right thing. He's responding to Patel's reaction to it.
It's okay for people to be ambivalent, or to have an opinion on only some aspects of an issue. Not everything you see is Red Team vs. Blue Team.
(He also kind of addressed some of your other points in the article as well, but perhaps not to your satisfaction or as directly as you'd like.)