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Roofstock, which has overseen more than $1.6 billion in transactions since it was founded in 2015, allows Pickens and other users to choose rental properties with varying degrees of expected returns, based on numerous risk factors, including location and tenant history. (Each listing contains extensive photos and inspection records.) Pickens picked up his first buy, a duplex in Memphis worth $129,000, a year ago, putting 20 percent down. After taxes, management fees—a property manager recommended by Roofstock oversees the building—and the mortgage payment, he makes roughly $200 a month. He’s already picked up five buildings in five other markets and spends less than an hour a week operating his property empire. It’s so easy he compares the process to fantasy football; Roofstock’s 30-day property return policy makes it “like buying a pair of shoes.”  Silly or smart?