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At some point Darius says Tom didn't seem to do a lot of reading people, the way he did when they first met. Wonders about that, and about his other skills as a jack-of-all-trades. Aside from making coffee and a bit of swordfighting. Tom says most of his skills were never needed. As for reading people, it works best on average people; for most of their journey, the people they dealt with were either just as skilled at hiding what they were thinking as he was at reading people, so he couldn't completely trust his readings, though if he'd ever suspected someone was lying about anything, he would have mentioned it.
At some point, Darius says real life isn't like fantasy stories, where the enemies are usually pure evil. In reality, their enemies basically have good intentions, even if they're misguided. And the Land certainly isn't a dystopia. And of course, the whole situation is open to interpretation; some may well see the Chaos as the bad guys, and they're not necessarily wrong. We might be the misguided ones. There's good and bad in everyone, after all, and it can be hard to tell the difference, sometimes.
Someone probably says "one person's utopia is another's dystopia." Maybe a streetrat spirit-talker?