Chicago · 2 to 4 unit buildings
Start with one question: what do you own? An agent who house hacks, or owns small buildings themselves, will answer in seconds. That answer tells you more than any website.
First, the words. House hacking means buying a building with two, three, or four apartments, living in one, and renting out the rest. The rent covers a big piece of your mortgage. In Chicago, the buildings made for this are everywhere: the 2-flat (two apartments, what most of the country calls a duplex), the 3-flat, and the 4-flat.
An agent who has lived in their own small building has picked which unit to live in, found their first tenant, and watched the rent land on the first of the month. They know which questions matter because they have asked them with their own money. Plenty of good agents sell houses. Far fewer have house hacked one.
Ask every agent you interview: What do you own? How many buyers did you help house hack in the last year? Can you walk me through the numbers on a live listing right now? If the answers come easy, you have found a real one.
One honest note about the job: your tenant is also your neighbor. Most owners find that makes things easier, not harder. Problems get caught small, repairs happen fast, and good tenants stay because the owner is right there.
If house hacking is on your mind, reach out. The first conversation costs nothing, and you will leave knowing your next step. You are closer than you think.