Dan Loves HousesCompass · Chicago

Chicago · 2 to 4 unit buildings

How Do I Start Buying My First Rental Property in Chicago?

You start with a conversation. Not a loan application, not a big savings account, not a five year plan. A conversation, and it costs nothing.

That surprises people. Most first time buyers think there is a gate to pass before they are allowed to talk to anyone. There isn't. Plenty of the people who reach out to us have never bought anything and are not sure they ever will. That is a fine place to start.

The hardest part is not the money

After more than 20 years of buying rentals and flipping properties, we say the same thing to every new buyer: the hardest thing about buying your first property is getting over your own fear. Not the down payment. Not the market. The fear.

The internet does not help. Every feed is full of reasons to wait. But the actual steps are few, and none of them are scary.

Step 1: Talk to us

Tell us where you are, even if where you are is curious and nervous. We will tell you what buyers like you are doing in Chicago right now and answer whatever you are wondering about. There is no cost and no commitment. Read our reviews and you will see the same words over and over: patient, no pressure. That is the whole approach.

Step 2: Go stand inside real buildings

Fear feeds on the abstract, and it shrinks in a real kitchen. Go to open houses on Sundays. Walk through a two unit building, the kind most of America calls a duplex and Chicago calls a 2-flat. See what $600,000 buys in Avondale, then see what it buys two miles away. In Chicago the spread between neighborhoods is the real story, and you can only learn it with your feet. Nobody expects you to make an offer. Looking is free, and it is the fastest way to turn "someday" into "that one."

Step 3: Learn to run the numbers

A building stops being scary when you know what it earns. We would rather teach you to run the numbers than run them for you, because the goal is for you to spot a good deal on your own. That is what our deal analyzer is for. Put in a Chicago address and see what a 2-flat, 3-flat or 4-flat would rent for, what it costs to run, and what is left over each month. Run ten buildings and the fog starts to lift.

Owning a building is real work some months. A furnace dies. A unit sits empty for six weeks. The numbers are how you plan for that, so a bad month is a line item instead of a crisis.

Step 4: When you are ready, talk to a lender

Notice this step is last, not first. You do not need a pre-approval to talk to us or to walk an open house. When you are ready to get serious, a lender will tell you your real buying power. If you plan to live in one of the units, you can often put 5% down on a building with up to four units. FHA can go as low as 3.5% down on a two unit building, though it comes with extra rules, which is why some buyers take the 5% route anyway. On a $600,000 building, 5% down is $30,000 plus closing costs. Real money, but a long way from the fortune most renters assume they need.

And here is the part renters never see. From the first month, your tenants' rent helps pay down your loan. It works like a 401K match at a job. It builds for you in the background while you live your life.

You are closer than you think

Nobody feels ready to buy their first building. The people who own them now didn't either. They just took a small first step, and the first step is not brave. It is a conversation.

Reach out. You don't need to know exactly what you want yet, most people who reach out don't.

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