Chicago Property Management Blog

This new federal tax bill passed in July is one of the most important shifts Chicago landlords and real estate investors have seen in years. Whether you own a two-flat in Avondale, a portfolio of rentals in the suburbs, or you’re eyeing your first multifamily, the details in this “Big Beautiful Bill” directly affect how you buy, sell, and manage property.Why should landlords care? Because taxes hit your bottom line jus...

For years, you’ve heard us saying that retaining good tenants will maximize your return on investment property. Maybe you didn’t believe us when we said that turning over a rental home when a tenant moves out significantly eats into your ROI. Rather than just saying “trust us,” we’ve brought our data to back up our recommendation.Windy City Turnover ExpertsSince 2022, GC Realty & Development, LLC has ha...

Let’s skip the small talk and go straight to the headache: property taxes are shifting under your feet. If you own rentals in the City of Chicago or anywhere in Cook County, what you pay (and when you pay it) is evolving, sometimes quietly, sometimes loudly, and almost always at the worst possible time for cash flowIn the last year, we’ve watched property tax timing slide (again), city fees and taxes shuffle, propo...

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...