A good shill won't always toe the line. That would be too obvious.
A shill should levy just enough dissent to retain some credibility among the most credulous. Usually by piling on to obviously losing causes. For instance if someone were an Apple shill, saying that the App Store review process is broken, the royalty split is untenable, XCode is shite and Apple's AI has been pretty bad are all obvious positions to take. These are blatant, undeniable positions.
Someone could have those public positions and still be a shill.
Is Gruber a shill? I mean, he seems entire dependant upon the Apple fanbase[1] for his income, and a lot of his credibility comes from access that Apple directly grants him. They give him products. He gets to host his "Talk Show" live at WWDC. He has done a number of interviews with Apple executives. He seems pretty firmly attached to the Apple teat and they serve up a supply of nutritious milk for him.
The base post was flagged, presumably because it used the shill label, but it's pretty hard to get away from it. And maybe that's perfectly fine, and the industry has a lot of shills for different things and we all factor in where they're coming from. Most HNers expect a "rose coloured glasses about Apple" perspective from Gruber, so it is weighted against the content.
[1] The Apple fanbase are a subset of Apple users. I'm typing this on an M4 Mac. My iPhone and iPad sit beside me. I'm a subscriber to Apple One Premier. Yet I'm not a fan. I don't, for instance, care at all how much profit Apple makes, much less excitedly gloating about what percentage of the market's profit they make. Nor do I get angry that Samsung copied some UI element or phone shape. Those are fan type topics.
(I'm too dense to understand your last sentence. :-) Sometimes when I take time to cogitate on a thing it will come to me though.)