pg hasn't changed a bit, as far as I can tell. Surrounding conditions (e.g. the political and media climate) have changed a lot, plus there are the expectations people have from anyone they perceive as rich and famous. He ignores that kind of expectation, which pisses a lot of people off—but this is nothing new.
Not changing when your environment changes is how everyone who is out of touch ends up well, out of touch. If Genghis Khan was still around roaming the steppes pillaging I'd hardly excuse it with "he's independently minded and ignores people's expectations, it just pisses a lot of people off"
This is btw another theme of the later batch of his pieces, implying what he's saying is valuable because he's such a maverick, has strong "wake up sheeple" vibes
That's a mushy pejorative; it means whatever you want it to mean. You could just as easily say he "thinks for himself"—poof, now we have a mushy honorific.
https://news.ycombinator.com/item?id=25233038