Been perusing the crap in the file more leasurely and something just jumped out at me in the final report. The vast majority of his unsecured liability is owed to the IRS.
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Our boy has not been paying his taxes and owes Uncle Sugar 150k. This answers the question as to how he was able to make his coin shop profitable. He was pretending he didn't have to pay the Danegeld. With a tax bill this large, he was probably doing it for years. We could possibly see a Prison arc in his future unless he manages to make our benevolent overlords very happy with the sale of his property.