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Why doesn't the enemy trigger the quest and release the hero?
The quest is triggered, but he can't release the hero due to the hero limit being reached.
Added 5 minutes later kolotok
I understand the idea is to keep the starting hero (attack the enemy hero and retreat). But why is he needed if there's no Wisdom skill (to spend the night near a tavern and buy back defeated heroes)?
Actually, although it's not obvious, Mr. Fat is needed to buy back escaped heroes later (not just Vertigo on day 121). Plus, he grants Vertigo the Blind skill. Without Blind, some battles might be impossible to win.