Cook County property taxes are the line that breaks pro formas: assessments move, appeals are routine (budget for the appeal itself), and the post-purchase reassessment can reset your math. Model taxes forward, never trailing.
If you own a two-flat or larger with owner-paid heat, winter gas is a four-figure season. Add snow removal (liability, not luxury), frozen-pipe risk in vacant units, and the boiler's service-and-eventual-replacement cycle.
Tuckpointing on a 15-25 year rhythm, lintel repairs, and wood porch systems that the city inspects — these are thousands-not-hundreds items that vintage-building owners must reserve for.
Tenant retention through responsive heat and maintenance (turnover in February is misery), annual tax appeals, and preventive masonry care. Chicago rewards boring operational discipline.
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