Possibly a Idiot.
I'm also going to have to edit the backstory a bit.
285 would be my first pick, but that might be too short of a time, depending on the turnaround on prisoner admittance.
What is the normal rate of admittance for prisoners? Every month, quarterly, semi-annually?
@Snarf Zagyg great choice of an uncommon item.
@FitzTheRuke Just confirming that you're fine leaving the Hermit Discovery fluid at this time. I am content to be surprised by it, if you like, or we can discuss offlist (DM or whatever). If you want me to adjust the extra language (from Goblin) that's also fine, or to a gambling tool if there is a game that the prisoners regularly play.
I'd also like to spend my only 5gp on a leatherworker's tool kit, if that's okay.
Number 6, you say, hmm?
You picked Number Six subliminally then, perhaps.