Chicago · 2 to 4 unit buildings
Use one filter and the list gets short fast: find an agent who owns small multifamily buildings themselves.
First, the words. A multifamily home is one building with more than one apartment inside. Chicago's small ones have their own names. A 2-flat has two apartments, a 3-flat has three, a 4-flat has four. Most of the country calls the two unit kind a duplex. Buy one, live in one apartment, and the rent from the others helps pay your mortgage. That is why the right agent matters so much here. You are not just picking a home. You are picking the person who teaches you the building.
An agent who owns a 2-flat or 3-flat has priced a roof, signed a lease, and taken the call when the sink leaks. They read a building the way an owner reads it, and they can tell you which block their own money would go to. Plenty of good agents sell houses. Far fewer own the kind of building you are trying to buy.
Reviews written by investors are the fastest tell. Read an agent's reviews and look for words like 2-flat, house hack, rental, and out of state. Buyers say what the agent was good at.
Investor meetups work too. Chicago has active real estate meetups, and buyers there name their agent without being asked. A name that comes up twice in one room is a real lead.
Then interview two or three. Ask each one how many 2 to 4 unit buildings they closed in the last year, what they own themselves, and to walk you through the numbers on a live listing.
A real multifamily agent opens a listing and shows you four numbers: what the units rent for, what the building costs to run, what the loan costs each month, and what is left over. The best ones teach you to run those numbers yourself, so you can spot a good deal on your own. That is how we work. They also know the local homework, like checking the city's records for how many apartments are legal at an address, and they hand you the lender, attorney, and inspector who do these buildings every week.
One more thing that surprises people. Live in the building and a regular loan goes down to 5% on buildings up to four units, and rent from the other apartments can count toward what you qualify for. The right agent knows the lenders who close those loans every month.
We are happy to be one of your interviews. Ask us what we own. Reach out, and bring a building or bring nothing. You do not need to know exactly what you want yet. Most people who reach out don't.