I think these are all fair points, and if the author of that article were capable of making them, I'd be sympathetic. Instead we got a litany of non-libertarians (including Larry Page! lol) plus David Sacks. Peter Thiel is also guilty, you see, because he's buddies with Sacks and once upon a time worked with Elon.
The underlying problem here is the naturalistic fallacy. Libertarianism is a set of statements about how the world should be, not about how it is. I think this is a flaw with the ideology, because I don't see a path from the "is" world to the "ought" world, but that's beside the point. Your chess vs checkers analogy is right on.
David Sacks had a concise statement about what he thought the world should be based on what it is.[0] I'm not sure how it works in practice, but it is a coherent worldview. Given that we don't live in a world corresponding to his proposal, but in one where certain people making loud noises can get their way, I don't see any hypocrisy, even though it may be embarrassing.
Thanks for the upvote – I'm at -3 so far. :D
[0] https://mobile.twitter.com/DavidSacks/status/163436339349803...