Are there any real life analogues to the Valyrian imperial system of having both provinces ruled directly by the “Freehold” and semi-autonomous colonies like the Free Cities? As far as a I can tell, aren’t colonial governors usually appointed by the imperial government. I know there was something similar with Salutary Neglect in the Americas, but what about the ancient world?

Yeah, it’s pretty similar to how the Romans managed their overseas affairs early on – you had certain regions that were provinces ruled by a proconsul, but you also had semi-autonomous kingdoms under Rome’s protection who paid tribute but ruled themselves, etc.  

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