This is really quick while I'm on my half and we'll see if I have the energy come back and elaborate more later tonight but an issue I've run into a lot with the sort of meta-read of the setting + trying to reconcile it with playability is, like

An inmate can have any read on the setting they want, and whether it's valid or something obviously way off base they have to overcome, they don't icly have any choice about it. Which DEFINITELY can have its own hurdles, but there's at least a very solid reason to keep them there. Whereas if a warden is repeatedly hammered with "everything here is bad and you are part of a corrupt/shitty/etc system", or things that make them doubt whether their windfall is some kind of trick, there's no cushion for keeping them here — and especially since wardens are likely to care about that kind of thing, it becomes this ooc wall of "my character either has to avoid or completely shut down the concerns of someone trapped and frightened/angry, or I have to grasp for whatever straws can maybe keep them from voluntarily leaving"

Or like, fixating on the system, which can be fun and viable, but not long term unless the goal of the arc is to see it be a failing effort or change the game radically

I don't know that I think there's any Right Or Wrong way to play it, I don't have A Solution, but this is a quick two cent explanation of why at least I specifically also kind of struggle to engage with this