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Then handle the NPC that comes out of it, and you'll be able to give him a job.
Seems like the Brothel is the better choice though, I totally missed those quests in my playthrough but it sounds like they NEED that position filled, whereas the Apothecary thing is like, more hobbyist or something.
What's better for Hugo though? No clue.
Not if you go there right away and do him in yourself. Then he'll show up right as you finish wiping your sword clean and, well, he'll be okay with it actually.
But you've gotta go pretty much as soon as you're informed about the prison break or you are indeed screwed. Though perhaps a wakestone can help, I dunno.
I also think the brothel guard is a better outcome. Like you said, they need protection after Wilhelmina leaves, and "unruly customers" doesn't sit right with me in that kind of establishment.