Should be some Urchins for sending purposes in the Ill Companions camp, or even desperate older folks who will run the errand for you.
It would be smooth!
There's already an IC plan to attempt to do this very thing.
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I think it's a good idea.
It seems entirely reasonable that the ill companion hobo's would do anything for money.
But you should have to pay something up front to an NPC like in Old Stones or be a member of their faction.