He never does his homework. That is why he is the bankruptcy king. He doesn't really care about running anything, and has no real ability for that sort of things. He just likes money and the trappings of power. He has found that any project that has a cash flow has massive potential for skimming, graft, and corruption which he is very good at. At the end of any project, he stiffs everyone that he can, declares bankruptcy, and looks for something else with cash flow.
Like laundering money for the russians.
Generally he makes decisions based on his enormous gut. Much like a dog. Should he eat it, screw it, or urinate on it. Sometimes he does all three, at least according to the russian hookers.