I’ve been managing rentals in Chicago and the south and west suburbs for over 35 years. I run a large portfolio here, and I list and sell investment property as a licensed Illinois broker. So when investors from California, New York, Florida, and the coasts call me chasing cash flow, I tell them the same thing I’ll tell you.
Chicago still pencils. But only if you buy the right building, in the right pocket, and actually manage it well. That last part is where most out-of-state deals fall apart.
Here’s what I see go wrong. An investor buys a “cash flowing” two or three flat off a pro forma, hands it to a manager who doesn’t really know these neighborhoods or the voucher process, and six months later the rents aren’t collected, the unit failed inspection, and the cash flow they were promised never showed up. The deal wasn’t bad. The execution was.
What I do is both halves. I help you find and buy the right asset, and then I manage it so it actually performs. That includes the Section 8 side, which is a big part of how you get real cash flow on the South and West sides. I handle the CHA voucher process start to finish, the RTA, the HAP contract, the inspections, getting units rent ready and passing the first time instead of bleeding money on re-inspections.
The play I believe in is simple. Buy a building that isn’t performing yet, stabilize it, get the right tenants in at the right rents, and then you’re holding an asset that cash flows whether or not the market appreciates. If you ever want to sell, you sell from strength instead of dumping a distressed building for pennies.
I’m not interested in selling you a dream. I’ll tell you straight if a deal doesn’t work. But if you’re sitting in an expensive market watching your margins disappear and you want boots on the ground in Chicago who can find it, fix it, fill it, and run it, that’s what I do every day.
Happy to talk through what I’m seeing in specific neighborhoods if you’re researching the market.
Mike Fisher
Illinois Licensed Real Estate Broker
M Property Group LLC / MF CashFlow Property Management
New Lenox, IL
