Chicago · 2 to 4 unit buildings
Here's the part most people miss: the age is the good news. Chicago's brick two flats and three flats went up when land, labor, and materials were cheap. Nobody would build them today. The brick walls, the thick old lumber, the tall ceilings, you cannot order any of that new at a normal price. So the real question is not whether a 100 year old building is worth buying. The real question is what shape this one is in. And that turns out to be a short, known list.
Old buildings have one more thing going for them. A 100 year old building has had 100 years to show you what it does. Nothing on the list below will surprise a good inspector. Here's what gets checked, and what a fix roughly means.
The roof. Many of these buildings have a flat roof, and flat roofs get redone every couple of decades, not once in a lifetime. Ask when it was last done, and look at the top floor ceilings for stains. A tired roof is a normal line item. A roofer can price it in a day, and that number can go straight into your negotiation.
The porch. The wood back porch is pure Chicago, and the city has real rules for it. The city requires porches to be built to hold 100 pounds per square foot, and repairs to structural parts, like columns, beams, and floor joists, need a city permit. So have your inspector look hard at the posts, the stairs, and any wood near the ground. A worn porch is a number, not a mystery. Crews rebuild these porches all over the city, and a porch bid is one of the easiest big items to price before you commit.
Electrical. Ask the age of the panels and the wiring, and count the outlets in each room. Some vintage buildings still run on small panels or original wiring. Electricians upgrade these buildings every day, and it can be done in stages, a panel first, circuits later. You do not have to fix 100 years of wiring on day one.
Plumbing. Two pipes matter: the ones in the building and the one to the street. Original galvanized steel water lines rust shut slowly, and weak water pressure at the top floor tap gives them away. For the pipe to the street, spend a few hundred dollars on a sewer scope, which is a camera run down the sewer line. It tells you about the most expensive pipe you own before you own it.
Foundation and brick. Brick needs tuckpointing now and then, which just means fresh mortar between the bricks. That's maintenance, like painting a wood house. What you actually want your inspector to check is movement: big cracks, bowing walls, doors that won't close. Old cracks are often cosmetic, from settling that finished decades ago, and an inspector can tell you which kind you're looking at.
Water in the basement. Look for water stains on the basement walls and floor, and ask the seller about it directly. A lot of basement water starts outside, with clogged gutters and downspouts dumping rain next to the foundation. Those fixes are cheap. Bigger fixes exist too, and a good inspector will tell you which end of that range you're on.
The inspection is where you win. Every item above gets priced before you're locked in. In Chicago, offers are normally written with an inspection period, so you inspect after your offer is accepted, not before. Illinois licenses home inspectors through the state, and a good one will walk the building with you and explain what's routine and what's real. Then you have three clean options: ask the seller to fix it, ask for money off, or walk away.
That flips the whole thing. The inspection isn't a test the building has to pass. It's how you buy a 100 year old building at the right price for its actual condition.
We help people buy these buildings all the time, with 20+ years of buying rentals and flipping properties here, so we know which items are routine and which deserve a harder look. If you're curious about a vintage two flat, or just wondering whether this kind of building could work for you, get in touch. You don't need to know exactly what you want yet. Most people who reach out don't.