Dude is smart, buy for pennies on the dollar, rehab, make money. Business mans dream. I have worked with people like him at first you look at it and go what is this person thinking ?? Then you watch him for 30 years and realize there is a reason he is where he is and doing what he is doing.
And if for some reason it does not work out he is sitting on millions of dollars of real estate. He will probably come out ahead.