the Libertarian/Anarchist philosophy tends to fall apart, because it assumes a level of intelligence and engagement that many people neither care about nor particularly want
That's a good critique, but I think it really hasn't been shown or demonstrated yet. Even with Dan leaving, I'm hopeful Steemit can play a role it showing people what it might look like with agorism, self-banking, smart contracts, secure communications, etc. Technology makes much of government obsolete.
Well, you may be right... and I like the way Steemit is a "soft sell" to get more mainstream people involved in something they'd mostly reject as "black box fringe dweller stuff."
To me, the best "pitch" here is that Steemit offers a return to more engaging "social blogging" for those who have grown tired of Facebook/twitter soundbytes, without deeper engagement. Then, as a fringe benefit, you also get introduced to the world of alt. economics and greater self-reliance. The average person on the street hears the word "anarchist" thinks of people dressed in black throwing molotov cocktails at demonstrations... and immediately reject the idea as "not part of any reality I want."
So I am hopeful, on the soft sell angle. And I'm hopeful that those of us who care can create a "model city" of sorts, here with Steemit.