Real Estate Broker · Chicago and Kansas City · Member since 2016 · 108 posts · 98 votes
Mine took about 3 hours a week across 22 units. A turnover (one tenant moves out, the next moves in) eats a weekend, and the rest of the time it runs on a system: one platform where tenants message me and pay, and tradespeople who bill me directly once I introduce them. I am curious what other Chicago landlords run. How many hours do yours take, and what is the one habit that keeps it low?
At 236 properties, the hours are not the point — the system is. If everything runs through you, the portfolio owns you, no matter how many doors you have. The habit that keeps it manageable is clear expectations up front and tight communication early. Tenants know how to pay, when to pay, and how to report a problem. For second-chance tenants, that means double deposit and biweekly payments aligned to paydays, watched close at the start. Turnovers and rehabs get a checklist, not memory. I spend my time on deal flow, numbers and exceptions, not routine messages that a clear process should handle.
