I've seen worse. My coworker and I had been booked into an AirBnB once, as hotels were all full. We've been told "One bed and one couch" - not good, but works in a pinch. Wrong. It was one double bed in the flat of an absolute, over the top gay males couple. Not only was the double bed a thing we would not accept, but the worst was that the room was all over decorated with pictures of naked men. NOPE. Not our style.
So we went bed-hunting, and were extremely lucky to find two hotel rooms that had been cancelled by someone else that day. When we sent in the invoices to the accouting department, they were not happy - Why would we book hotel rooms if there was a booked and paid AirBnB? I sent them two photos I had taken of the AirBnB room, and they paid the hotel bill without any more questions.
When will he learn that this is not one of his crooked deals, but a "pay up or shut up" situation? I hope he'll have to sell his real estate pennies to the dollar.
What will happen if everything is sold and he is still in debts?