Active or Open Games
More than anything else the so-called "Freebooter Strongholds" are shaped by their geography. Though the Starlost Mountains rise rather abruptly from the flatlands of the Great River Conclave the same is not true on their western side where the lands are hilly and broken for a fair distance from the mountains proper. It is these lands which shaped the culture of the Strongholds.
Within this culture the custom which most infuriates the more civilized lands is the "Right of Passage." According to this custom no one is permitted to obstruct a traveler. Among other things this "Right" completely forbids any form of slavery, serfdom, or debt bondage. Though the laws against piracy are enforced in these days, the "Freebooters" retain that name because they refuse any and all claims to property in persons, infuriating slave owners and serf overlords (and certain parents) whose "property" has traveled to the Strongholds.
Individually, the Strongholds vary greatly in size. This is mostly dependent on the quality of the roads. Where high quality roads have managed to be built, alliances have tended to increase the territory under a single government. Where there are poor quality roads a single valley might be completely independent. Though the roads do vary greatly in quality (and local guides are often needed), heavy wagons can travel the complete distance from the Sunken Circuit in the north to the Sea of Durmstrang in the south.
Governments in the Strongholds grow by alliance and intermarriage. While raiding is possible (and some would say frequent), major assaults, either internally or by outsiders have proven almost universally ineffective.
The Kolob (as the people of the Strongholds call themselves) are masters of Astrology. This seems to be the source of the Right of Passage - obstructing a traveler would go against the stars.
Amazing how an obsession with the chaos of freedom comes from one of the most ordered and confining of disciplines.