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Since you are leading this raid, you get to make the decision that some infiltration is in order first. If you can scout out the enemies defences, and maybe find where they keep all the valuable stuff, then the raid will go better. Almost as if its some kind of secret DC to it. Handcock disagrees and attempts to usurp your authority, he wants to simply attack now! But Dave has your back, so he loses the 2v1 vote.
Using your dark magic, you fashion up some disguises for you and Dave. Hankcock refuses to be a part of your magical shenanigans, choosing to stay behind with the men. He gives you a horn if you need backup, blowing the horn will trigger the attack early.