Two-flats are the most common building type we source across the South and West Sides. They are also the type where a fast, structured assessment saves the most time — because the failure modes repeat.
Start with the envelope
Roof, masonry, foundation and windows. These are the items that are expensive, non-negotiable and easy to underestimate from photographs.
Chicago masonry buildings frequently need tuckpointing, and a parapet in poor condition is a materially larger job than it appears. If the building has a flat roof, its age and how it drains are among the first things to establish.
Then the systems
Electrical service and whether it is knob-and-tube or updated. Plumbing, particularly whether the supply is galvanised. Heating, and critically whether units are separately metered or the building is on a single boiler.
Separate metering matters more than most new investors expect. A single-boiler two-flat means you pay heat for both units, which changes the operating numbers substantially.
Establish the legal unit count
A building marketed as a three-unit is sometimes a legal two-flat with a non-conforming basement unit. That distinction affects financing, insurance, and what you can lawfully rent.
Check the zoning and what the county records show rather than relying on how the property is described. This is one of the most common and most expensive surprises in Chicago multifamily.
Rents, not rent estimates
If the building is occupied, ask for the actual rent roll and whether there are written leases. In-place rents below market are an opportunity, but only if you can realistically reset them — which depends on tenancy, timing and the local ordinance.
If it is vacant, base your projection on comparable units in the same few blocks rather than neighborhood averages. Chicago rents vary sharply over short distances.
Taxes
Cook County reassessments can move a property's tax bill materially, and buying at a price well below the assessed value does not automatically reduce it.
Underwrite the tax line on what it is likely to become rather than what it was, particularly if the property has been under-assessed.
Then decide quickly
The point of a structured order is speed. Investors who look at many buildings in a small number of markets can work through this in well under an hour and give a firm answer, which is exactly what makes them the buyers who get called first.