Everyone loves to say "sold at a loss", as if that's the dumbest thing about it. It's much, much dumber than simply selling at a loss. When he bought the property, the backyard was just grass and the basement was unfinished.
Pool and hot tub installed in the yard and then later, brick grilling station, all running off a buried propane tank for the hot tub heater. Custom made bar and high end theater room. Motorized seats, Crestron controls. Wooden, refrigerated wine cellar. Custom built gun closet/safe room. Custom made desk for his office which was decorated with hand carved molding. High-end furnishing for three guest bedrooms. Weekly housekeeping and grounds keeping crew. A service that decorates your house for the holidays then takes it down and stores it until next year. Plus $60K/yr to Keith's wife to manage the house/shop/do laundry.
It's not just "selling at a loss". He sunk easily over a million dollars into the property post purchase, and THEN sold at a loss from the original sale price in 2006.
He put in a combo pool-hot tub, theater, BBQ, buried a propane tank, safe room, etc. The buyer got all that for FREE and got the property at a discount. Makes me wonder how broke he was going to bail on an over the hill mortgage just for the equity. I don't care how much you hate "NYC", you don't live in NYC, you live in a very fancy neighborhood, far, far away from any riff raff. Why would you give all that up for some cramped swamp house. Now you don't even have your wackpack friends.