When selling a Chicago 4-12 unit actually makes sense (even if it cash flows)
Most real estate advice says “never sell a cash-flowing multifamily property.” In Chicago, that rule is not applicable more often than people admit.
I own and manage multifamily here, and I’ve watched otherwise “good” buildings quietly underperform once you factor in:
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Property taxes rising faster than rents
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A real CapEx cycle approaching (roof, tuckpointing, boilers)
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Management intensity that no longer matches the return
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Equity growing while cash flow stays flat
I’ll add this because it’s relevant: I’ve personally sold a Chicago 4 unit building in Rogers Park that was cash flowing.
Not because it was a bad property—but because once I ran the keep vs sell math, the return on equity no longer justified the management, upcoming CapEx, and risk compared to other options.
On paper, the building worked. In reality, the capital was better deployed elsewhere—and that decision improved my overall portfolio performance.
When I evaluate a sale, I don’t ask “does it cash flow?” I ask:
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What is my true return on equity today?
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What CapEx is realistically coming in the next 3–5 years?
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Is this asset still doing what I need it to do for my portfolio?
Sometimes the right answer is holding.
Sometimes it's selling before the decision is forced by taxes, CapEx, or burnout. (lol, we all know that happens as a landlord)
If you own a 2–20 unit in Chicago and you’re holding a cash-flowing building but questioning whether it’s still pulling its weight, that’s usually the right moment to run the numbers—calmly, not reactively.
Happy to talk it through.