The anarcho-syndicalist flag with the Circle A superimposed over it, the latter originating from the International Worker's Association
So via Tenkar's Tavern I found a link to an interesting blog. Anarchy Dice is available as both a blogspot and now as its own website.
I'll be sure to update the list over time when new posts come in.
One of the interesting features I found was a series of posts about anarchist settlements in a D&D world, and what kinds of interesting features they may have for traveling adventures. The blogger asserts that the common pop culture conception of anarchism as "strong rule the weak, no rules for anyone" is an inaccurate perception which a lot of RPGs propagate. Eclipse Phase is a very notable exception. The author himself is of the anarcho-capitalist grain, but acknowledges the different sub-sections of ideology and attempts to write up examples in a respectful way. I generally don't talk about political stuff on this blog, but I may make exceptions in regards to how they can be used for a better gaming experience and trends in gamer culture.
Origins of Anarchism
The original ideology of anarchism was formulated in the 1800s which viewed the State (be it a government, monarchy, or company town) as an oppressive system which created a hierarchy of haves and have-nots. The ideal society for anarchists would be voluntary associations of people bereft of such systems. The earliest known themes are dated in the writings of the Taoist philosopher Laozi, but anarchism in its modern form sprang from Enlightenment thinking and the political turmoil of Europe in the 18th and 19th centuries. Far from a fringe group, by the late 1800s anarchists were a force to be reckoned with in Europe. The ideology had popular followings in worker's unions, and political activism helped normalize the 8 hour workday in the Western world.
The bomb-throwing stereotype came due to anarcho-nihilist militants bombing noble estates in Russia, plus violent clashes with the police in the US and Western Europe over worker's rights and wages. The Haymarket Affair is probably the most famous example of this.
And this is where it gets interesting: over the past century and a half, you ended up with varying strains of anarchist thought on how to best achieve an ideal society and fight the State. You had anarcho-communists, who advocated for the abolition of the State and capitalist businesses in favor of common ownership over the means of production. You had anarcho-syndicalism, which held similar anti-capitalist leanings, but who focused mainly on the creation of democratic trade unions. Then you had anarcho-capitalists, who are the odd man out in that the original anarchists were strongly anti-capitalist in a time when robber barons, child labor, and debtor's prisons predominated. And that's not covering the more obscure derivations, such as Christian anarchism which recognizes only the word of God and no human government as legitimate authority.
Apologies for the monologue, but in spite of not being an anarchist I overall find it to be a very interesting ideology, and I think that this understanding can be useful to get a better sense of the blog posts instead of diving in unawares.