Spellbooks are not easily replaced. A greatsword fighter can just buy another greatsword the first time the party reaches a town. The wizard can buy a blank spellbook, but what good is that? You've still lost all your non-prepared spells. Even if you capture another wizard's spellbook, it won't have the same spells in it; wizards pick the contents of their spellbooks carefully.I wager GR and WotC are smart enough to make sure that PCs can get the needed items (spellbooks, focuses, and tools) as well as some decent armor and weapons, but the trope has a lot of "bad" experiences because a lot of DMs think its a better "challenge" or "more realistic" to not be able to cast spells, use skills, or have an AC higher than 13 and do more than 1d6 damage per hit.
I'm not saying it's impossible to do a "start in prison" scenario well, but I don't think I've ever actually seen it done well.
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