Let’s be real for a moment—no one invests in Chicago real estate with dreams of sitting through eviction court. Whether you’ve got a vintage two-flat in Humboldt Park or a six-unit walk-up in Pilsen, every landlord has one thing in common: the desire to collect rent without drama. But even in 2025, with all the tech, automation, and tools at our fingertips, we’re still seeing landlords caught off guard by the same preventa
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