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For years on her twice-a-week walks, architect Elissa Morgante would pass a rundown little shack on a wooded lot with a Jeep halfway buried in mud out front. The property sat next to a path to a beach right on Lake Michigan in the Chicago suburb of Wilmette, Ill. In time she worked up the courage to knock on the door, telling the elderly woman who answered that she’d buy the house in a heartbeat. The woman said she’d put Ms. Morgante’s name on the list.
Then, one day seven years ago, Ms. Morgante walked by again, only to…