Chicago Property Management Blog

For new real estate investors entering the Chicago rental market, whether you’re considering a two-flat in Logan Square, a condo in Hyde Park, or a courtyard building in Rogers Park, one of the earliest financial decisions you’ll face is whether to collect a security deposit or a non-refundable move-in fee from your tenants. While these two options may appear interchangeable at first glance, they are treated very differently...

Managing mixed-use properties that combine both residential and commercial spaces comes with unique challenges and opportunities. From handling tenants with different needs to ensuring compliance with zoning laws and lease agreements, successful mixed-use property management requires expertise and strategy.Chicago, in particular, has a large stock of these types of buildings. Whether it’s a property in suburban downtown areas like...

Most investors think they already know the reasons to hire a property manager: someone to collect rent, handle repairs, and answer tenant calls. But let’s be honest, if those were the only reasons, plenty of Chicago investors would keep self-managing and never call us.The real reasons, the ones investors don’t consider, are actually far more powerful. They aren’t about convenience. They’re about protecting your i...

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...