Chicago Property Management Blog

The Big Myth Every Chicago Landlord BelievesMost landlords in Chicago think this: If I charge the highest rent, I make the most money.It sounds logical. Higher rent = more income, right?  Wrong.In our 23 years at GC Realty & Development, after leasing over 5,000 rental units across Chicago and the suburbs, we’ve seen this mistake cost landlords tens of thousands of dollars. The truth? Your rental price isn’t just a...

GC Realty & Development LLC manages over 6,000 rental units across Chicagoland. With all those doors, you can’t help but collect a few battle scars, plus tons of work orders.Recently, we sat down and counted them. Did you know that between 2022 and mid-2025, we completed over 31,000 maintenance work orders? That’s not a typo. That’s the cost of doing business when you manage properties in a city where the winters f...

Managing a rental property in Chicago comes with a set of legal responsibilities that every landlord must understand. Staying updated on Chicago’s property management laws is essential to protecting your investment and maintaining positive tenant relationships, whether you're managing properties on your own or partnering with a professional.In this blog, we’ll explore the key legal pitfalls that property owners often enc...

Hey Chicago landlords,You bought a rental property. That’s a smart move.Now you’re thinking:  “I can manage it myself and save money.”It feels good to save a few bucks, right?But here’s the truth:  You’re not saving as much as you think.  You’re just not paying yourself for your time. You Wear Every Hat (And Don’t Get Paid For It)When you manage your own rental, you do every...

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 t...

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...