Chicago Property Management Blog

In the fast-paced world of real estate, particularly within a market as competitive and diverse as Chicago, distinguishing yourself as a successful investor is a journey that requires more than just financial resources. After over 20 years of navigating the Chicago real estate landscape through being an investor on over 500 deals, operating Chicago’s responsive Property Management company, GC Realty and Development, and co-hosting...

Tenant screening in Chicago isn’t just about running a credit report, it’s about playing defense in a game where the rules are stacked against landlords who get sloppy. I’ve leased thousands of units, managed over 6,000 residents, and seen the same screening red flags repeatedly. Some are obvious, some are subtle, but all of them can cost you real money if you miss them.Let me walk you through the screening red flags t...

Every Chicago landlord has been there: the phone rings, someone wants to see your rental, and within 30 seconds of the conversation, you already know this prospect isn’t a fit. But if you don’t have a system, you’ll waste your time driving across town, unlocking doors, and listening to a story you could’ve avoided with five quick prescreening questions.Prescreening isn’t about being nosy; it’s about p...

These are the questions I get asked all the time by Chicago investors like you. Today, I want to share all of the answers with you about these investor questions.If you are reading this, you obviously care about putting the right tenant in your unit and you want to lower your risk, so kudos to that.  If you are reading this after you have an issue, this is still great info to know or read down to see if we can help.This Q&A gui...

Chicago landlords, let me hit you with something that should send a chill down your spine: the wrong tenant can cost you more than a year’s worth of profit on a single property.I’m not talking about little annoyances like late fees or phone calls about leaky faucets. I’m talking about full-blown financial wipeouts, months of unpaid rent, legal bills, city fines, and trashed units. If you think that sounds extreme, it&r...

If you own rental property in suburban Cook County(different in Chicago proper), you’re not playing by the same rules you were five years ago. Since June 1, 2021, the Cook County Residential Tenant Landlord Ordinance (RTLO) went into effect and reshaped the way landlords and tenants interact.And let me tell you, this isn’t the type of ordinance you can skim over or assume you’re “close enough” on. One small...

Tenant screening isn’t the sexiest part of being a landlord. Nobody buys their first two-flat in Avondale thinking, “I can’t wait to run background checks.” But here’s the truth: screening is where you either make or lose money.It is also where you set yourself up for easier management.  As a Property Management company owner, I learned over 20 years ago that if put 80% effort into marketing and screen...

Do you ever feel stuck when trying to pick where to buy rental property around Chicago? You see one suburb with cheap homes. Another with high rents. Some with confusing rules. It can feel like throwing darts blindfolded.You are not alone. Every week I get calls from investors asking the same thing:  “Where is the best place to buy in the Chicago market?”Today, I’ll give you the answer. And I’ll show you why...

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...