I don't actually have a good answer for your second question. It's a tricky one, which is why I wrote nothing. In the specific circumstance you describe I probably wouldn't bowl with the guy - heck, I've cut people off for far less (e.g., slut shaming in my presence). On the other hand, my cofounder is a big proponent of all sorts of things I oppose (Obamacare, basic income, extreme feminism) and I have no plans to cut her off.

I suspect the reason this jumped out at me is that it's literally an attempt to ostracize a hollywood writer for his other views, and being the good liberal that I am (culturally speaking) this jumps out at me.

So I guess at this point I'm walking away with far less certainty of my views than I started with.

As for the article, you are right that it's not position #1 good. It's a well written version of the same sort of fluff that HN has way too much of, nothing more.