Chicago Property Management Blog

If you’re a landlord in Chicago renting to Section 8 tenants, this update matters. I’m not here to scare you—but I don’t want you getting blindsided either.We’re about to hit a big shift in the Housing Choice Voucher (HCV) Program, and it’s going to hit your bottom line if you’re not prepared.Starting May 1, 2025, HACC (the Housing Authority of Cook County) is making some serious changes to...

It started with a great application—solid job, decent references. John thought he had found the perfect tenant for his Chicago rental. But within a few months, rent payments were late, complaints from neighbors started rolling in, and the property was showing signs of neglect. Before long, John found himself drowning in unpaid rent, legal battles, and mounting repair costs.As a Chicago property manager or landlord, stories like Jo...

Investing in rental property in Chicago can be a good opportunity, but understanding how to conduct a proper rental analysis is key to maximizing your investment. Whether you’re a seasoned rental property owner or a first-time investor, evaluating market conditions, rental rates, and operating expenses will help you make informed decisions. In this blog, we’ll explore essential factors of rental analysis, ensuring you maximi...

If you're a landlord or real estate investor in Chicago, you've likely heard about the controversial Northwest Side Preservation Ordinance. Recently, on Straight Up Chicago Investor, Brie Schmidt, managing broker and owner of Second City Real Estate, took a dive deep into this ordinance and its significant implications for property owners. She’s been a Chicago landlord for 13 years and has been an investor agent with her o...

Recently, Straight Up Chicago Investor welcomed back Tom Raleigh, founding attorney of Halsted Law Group. The last time Tom appeared on the podcast was Episode 40: Navigating Chicago’s Eviction Process. After four years, he’s back to offer practical tips and solid advice for landlords on Cook County evictions in 2025 and how to stay ahead of issues.Tom offers advice on the eviction environment in Chicago. He covers typi...

Screening tenants in 2025 isn’t just about filling a vacancy—it’s about protecting your investment and maximizing your profits. With changing laws, savvier tenant scams, and an unpredictable rental market, Chicago landlords need to step up their game or risk costly mistakes. A bad tenant means unpaid rent, legal battles, and property damage. But with the right system in place, you can avoid the headaches and find the r...

The shift to remote work has reshaped numerous industries, and property management is no exception. With more professionals working from home, the demand for rental properties with specific amenities, flexible lease terms, and better property management services has grown. As a property owner, you must adapt to these changes to stay ahead of the curve.How Remote Work is Reshaping the Rental MarketRemote work has significantly alter...

Investing in a rental property can be a good investment, but managing it effectively requires time, expertise, and resources. This is where professional property management services play an important role. Understanding property management fees and property management costs is essential for property owners like you aiming to maximize their investment returns.In this blog, we’ll explore the different property management fees r...

Why School Districts Matter for RentersFor families looking to rent in Chicago, proximity to top-rated schools can be a game-changer. Access to quality education is a top priority for parents, and living near reputable schools not only simplifies your daily routine, but can also enhance your child’s learning opportunities.At GC Realty & Development, we understand the importance of finding a home that meets your family’s ...

California’s wildfire crisis has revealed vulnerabilities in the property insurance market, with skyrocketing premiums, reduced coverage options, and new regulations shaping how homeowners protect their assets. While Chicago faces different challenges, such as extreme weather, flooding, and infrastructure aging, California’s situation offers valuable insights into how insurers respond to escalating risks and what property ow...