Chicago Property Management Blog

If you’ve ever asked yourself “Is now a good time to rent out my Logan Square condo?” or “How much could I get for my condo or apartment on the boulevard?”, you’re not alone. As a partner at GC Realty & Development and co-host of the Straight Up Chicago Investor Podcast, I field questions like these every day. After two decades of leasing homes in Chicago’s north-side neighborhoods, includin...

Those newer to investing in rental property in Chicago often assume their biggest cost is over after purchasing a new property. It’s true that the purchase cost may be the biggest amount they pay at once (but not always!). However, property owners need to prepare for many additional costs along the way.One cost that typically surprises property owners in Northwest Chicago is preparing a rental for a new tenant. Sometimes, the outg...

When you search for “property management near me” in Chicago, you’re not just clicking through Google results, you’re making a decision that will impact your largest financial asset. For most investors, their real estate portfolio represents the bulk of their wealth. Choosing the right property management company isn’t just about convenience, it’s about protecting and maximizing returns on your bigges...

When your rental property is functional, safe, and clean, you lease faster, attract better residents, pass inspections, and keep renewal rates high. Sounds like common sense, doesn’t it? To keep everyone on the same page at GC Realty & Development, LLC, we created the GC Property Standards™. This three-pillar approach sets clear expectations for rental conditions before we list a vacant property.We’ve created a pra...

The Chicago real estate market has long been a prime destination for investors looking for strong returns and consistent growth. With a mix of historic neighborhoods, rapidly developing areas, and a diverse economy, Chicago offers opportunities for both seasoned and first-time real estate investors. But to truly succeed here, you need more than just capital. You need strategy, timing, and a clear understanding of the city’s unique...

When we first hit record on the Straight Up Chicago Investor Podcast, we had no grand plan. We didn’t know whether it would fizzle out after 20 episodes or turn into something people actually cared about.  We did know that 90% of podcasts never make it past ten episodes so we made it a point to record eleven before we launched.   It started as a way to connect with other landlords and investors, share our experiences in ...

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...