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I think Jack's most grievous sins are represented by the "spirits" he sees.
The nude lady/old crone in ROOM 237 represents Lust = 2nd circle of Inferno
Lloyd the Bartender in the Gold Room represents Gluttony = 3rd circle of Inferno
Delbert Grady the butler/old caretaker/axe murderer in the Red Bathroom represents Murder = 7th circle of Inferno
each sin when matched with the number of it's circle in Inferno gives you 237
I think Jack even see's the spirits in that order.
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I'm convinced you have nailed it!