I think it's like any other form of governance in that it's subject to scope creep and the principal-agent problem. Even Bitcoin has to fight that. That's what sucks, another thing you're constantly having to fight just to maintain.

I'm president of a road association, and not by choice, old timer nominated me and no one else would step up.

Road is an HOA structure, but explicitly limited scope, and still have to deal with folks who want to assume expansion of that scope or nit maintenance projects upwards to socialize the cost of their wants.

What's the alternative? Road either becomes impassable-ish for lack of pooled maintenance funding, spend a small fortune just to move to a noisy public road with higher taxes, or lobby the town/county to assume control which will be even more work and expense.

It's tadeoffs all the way up and down that nobody wants to make. The irony is not lost on me that I'm an ideological AnCap miffed about having to maintain a private road.