Active Chicago investors look at 30–80 2-4 unit listings a week. You don't have 15 minutes per listing to underwrite each one. The skill is knowing which 5 data points to look at first so you can reject the obvious passes and only pull out the calculator for the maybes.
The scan, in order
Price-per-unit sanity check
Divide list price by unit count. For a Chicago 2-4 unit, the rough sanity band is $80,000–$180,000 per door depending on neighborhood and condition. If a 3-flat is priced at $480,000 ($160k/door) in South Shore, somebody's optimistic. If a 2-flat is priced at $95,000 ($47k/door) in Bronzeville, the rehab is going to be enormous.
The photos
Look at three things: kitchens, basements, roof/exterior. Kitchens tell you rehab scope. Basement photos (or lack thereof) tell you foundation and mechanical condition. Roof age is visible from the listing photo half the time. Skip the staged living room shots.
The remarks
Search the remarks field for these words: "as-is", "cash only", "investor special", "needs work", "motivated seller", "value-add". Each one is a real signal. Also look for: "tenant-occupied", "long-term tenant", "Section 8", "month-to-month". These dictate your acquisition risk.
The rent roll (or lack of one)
If gross rent is disclosed: divide by purchase price, multiply by 12, then divide by 100. That's a back-of-napkin gross rent multiplier check. Below 6 = expensive. Above 10 = either suspicious or distressed. If no rent roll: assume below-market and underwrite accordingly.
The DOM (Days on Market)
0–14 days: hot, expect competition. 15–60 days: workable, expect a price drop if you wait. 60+ days: either overpriced or the photos hide a problem. 90+ days in Chicago on a small multifamily means the listing has a story.
The decision
Pass / pull out / pursue. If you got two yellow flags or one red, pass. If you got one yellow, pull the address into Prop-Folio for the full underwrite. If everything looks right, save it and call the agent today.
The 5 red flags that should stop you
- No interior photos. Either it's a tear-down or the listing agent is hiding something.
- "Tenant currently in process of being evicted" language. Cook County eviction timelines are 4–8 months. Factor into carry costs.
- HOA dues on a 2-4 unit you can't verify. Common in condo-converted buildings. Can blow up your cash flow.
- Pre-1900 build year with no rehab disclosed. Could be perfect or a $200k surprise.
- Sold last 12 months. Check the prior sale. If it sold for $130k 8 months ago and is now $215k with no rehab, something's off.
What Prop-Folio does once you decide to pursue
Paste the address. The app pulls bed/bath, sqft, year built, market value estimate, per-unit rent comps, and tax data automatically. From there, a Deal Score across the 4 strategies tells you if the numbers actually work.
Underwrite your next listing →
Related: Chicago BRRRR underwriting · What is a Deal Score? · Rookie investor mistakes