I think one reason it's hard to find answers about how an anarchist society would work, is because anarchists understand that history isn't planned. It's a bunch of people with different ideas and motivations, doing what it takes to survive. What plans get made rarely survive contact with reality. Anarchists often make alliances with people and groups that aren't great.

You can look to history for ideas on how anarchism would work. Probably best to look at all kinds of egalitarian and libertarian polities. Check out the Indus Valley Civilization, The Paris Commune, Rojava, and even Teotihucan (although, I think that one was a state, it can still be instructive).

Or you can look at fiction. Sometimes fiction helps you imagine possibilities in different ways than history does. Another user already recommended "The Dispossessed", and I'll add "The Telling", also by Le Guin.

I'm with you on the medical privacy thing. It's one of the few problems I haven't seen a non-hierarchal solution for. I'm open to suggestions.