Isekai Meikyuu de Harem o - Vol. 2 Ch. 6 - Labyrinth 2

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Why not try to go to the second level? Normally if you can one hit kill the enemies on the first dungeon level, you wouldn't think twice about going deeper. But then again, we already knew this MC isn't the sharpest sword on the rack.
 
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He was considering checking another floor, but odds are unless he's in danger himself the rewards aren't going to be that much better per kill in there anyway. There's the matters of probably having to fight his way through the different floors to get to a more profitable one, using stamina and time on the less profitable enemies along the way. With the time constraints on getting cash for Roxanne, going for more of a "win the lottery on bandit bounties" approach might be a better option if both are potential risks to his safety anyway.
 
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@Glomoro Is taking down intelligent bandits with significant bounties really far less dangerous than unintelligent monsters? Realistically it should be difficult to even find wanted lowlifes. If the guards or the knights knew a wanted criminal's location, they would go in person to bring down the crook, not pay outsiders to do it. It should take a while to figure out where the hideout is. A dungeon, however, is full of monsters. You find them, whether you want to or not.
 
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Realistically it should be difficult to even find wanted lowlifes.

Great analysis. Let's see how it plays out in the next chapter. I really hope the economical sense is realistic (no hardcore plot armor).
 

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