I love the idea of this. But I do think that it needs another pass. the way it reads there's no reward for success except starting again and going until you fail. I doubt that was the intention.
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Thanks for the review! In my experience, players don't really fail montage tests so this one acts more of a subversive puzzle for the narrative than a real challenge. Was the montage test the right way to do that? Who knows. But, I imagine the players will already be suspicious and try to wreck the party fairly quickly after it becomes clear this is a "hotel california" situation.