Chicago Property Management Blog

Chicago property manager, investor, and real estate entrepreneur Mark Ainley has seen nearly every twist this business can throw at you. From house-hacking roommates in his condo to managing over 7,000 units across the city and suburbs, Ainley’s career spans 20+ years of leases, evictions, flips, and industrial deals. His lessons today are as practical as they are battle-tested.Let’s break down some of the best insights from...

Let me guess, you thought the worst was behind us after Friday’s downpour?In a matter of days, we’ve seen flash floods rip through the city’s South Side, flood basements in Bridgeview and Summit, shut down roads in Elmhurst, and leave landlords mopping up messes that insurance adjusters haven’t even gotten to yet.Now here’s the thing: flooding isn’t new in Chicago. It’s part of the deal when you...

Let’s be real for a moment—no one invests in Chicago real estate with dreams of sitting through eviction court. Whether you’ve got a vintage two-flat in Humboldt Park or a six-unit walk-up in Pilsen, every landlord has one thing in common: the desire to collect rent without drama. But even in 2025, with all the tech, automation, and tools at our fingertips, we’re still seeing landlords caught off guard by the sam...

You're sitting at your kitchen table, running the numbers on a two-flat you’ve owned for decades in Humboldt Park. You’re finally ready to cash out, retire, maybe head somewhere warmer. But your agent calls, and suddenly the plan comes to a halt. "We’ve hit a roadblock with the 606 ordinance. Title's not clean, lender’s pulling back, we may need to delay."This isn’t fiction. This is the re...

Between Landlords I talk to looking for Property Management at GC Realty or Investors on Straight Up Chicago Investor Podcast the desire for majority is just to make more money from your current investments.  There are many ways to add money to the bottom line and I see Chicago Landlords try tons of different stuff.  Here are a few ways I see Chicago Landlords try to profit to existing properties.Add solor panels(not proven to...

You know when you sit down with someone who's been through it, not just talked about it but really lived it, you end up having a way deeper conversation.  You dive into topics that are meaningful and create curiosity to pull out nuggets of what the other person knows. Well, at least it might be meaningful for Chicago investors.That’s the outcome I always get after spending time with Jared Kott of Marblestone Property Mana...

I am super excited about this article because I had an “ah ha” moment last week.  In 2014 we designed and built our own exclusive Property Management software and since then, we have been collecting a plethora of data points.  The data we have collected has helped us make informed decisions around ramping up hiring, planning seasonally, and forecasting maintenance costs. But we have kept all this data to ourselves....

The longer I do this, the more I am confident that an investor’s journey depends more and more on the resident they place in their unit over all other factors.  Even paying 20% over the market gets fixed long term.  Remember “Time Is Your Biggest Asset” as we say all the time on the Straight Up Chicago Investor Podcast. Want Better Tenants? Do This First.If you’ve ever had a tenant who paid re...

Top Landlords Are Doing This in 2025There’s a quiet shift happening in Chicago right now. It was fairly easy to become an investor between 2018 and 2021.  Interest rates were low, there was inventory, and rental rates were on the rise, even with the largest pandemic in over a century in the midst of it.During this period you have major shifts in how Chicago Realtors are conducting business with the NAR settlement, Cook County...

Between my role at GC Realty & Development & connections with investors around Straight Up Chicago Investor podcast the conversation around scaling comes up daily.  In the end everyone has 24 hours in a day but how do some investors grow faster than others?Buying the First Property Is Easy. What Comes After? That’s Where the Game Changes.Everyone remembers their first unit. Maybe it was a condo you lived in and decide...