Chicago Property Management Blog

Happy anniversary to us! After four years and 300 episodes later, the Straight up Chicago Investing is still going strong.  To celebrate our 300th episode, we took to social media to ask our community what questions they wanted us to answer. And you delivered! We received dozens. Unfortunately, we couldn’t answer them all in one episode, but we’ll make sure we do answer them somehow.So without further ado, let’s...

Chicago is one of the ripest markets in the U.S. for real estate investors, and that's no secret. According to research from RentCafe, 54% of Chicago's households are renter-occupied. For comparison, the national ratio is 34% of households occupied by renters. That's a whole lot of rental property!Don't start drooling just yet though. Whether you're new to the real estate investment game or have been around the block...

Remember that old saying that truth is stranger than fiction? Our friend and Straight Up Chicago Investor podcast guest, Joseph Pochinskas, found himself in the landlord twilight zone with his first investment property. A Southside Chicago native, Joseph fell in love with the Bridgeport/Canaryville area and decided that’s where he’d try his hand at house hacking. After a lot of research and walking properties, he settle...

Chicago real estate investors have long heralded the importance of cash flow from rental properties. Unfortunately, too many landlords focus just on the cash flow aspect alone. This can cause them to snap up properties that look like great cash cows but end up having problems that require paying out of pocket to solve. Others sit on the sidelines waiting the unicorn cash flowing purchases to fall into their laps. Both groups end up...

Disclaimer: In the following story, people moved into a rental home without permission or were scammed. When tenants move into a rental after being scammed by other shady people, they often move out right away and accept the fact that they fell victim to scamming. The people in this story did not. GC Realty & Development did not participate in the scenario below. Names have been changed and any likeness to another shady person ...

Being a Chicago landlord in 2024 is proving more difficult than ever. This is especially true when you inherit a tenant or make a huge mistake screening and you have to get a tenant out of your place. Many would-be real estate moguls hang up their dreams after dealing with evicting non-paying tenants. The legal system in Cook County, where Chicago is located, has always challenged landlords, even prior to COVID. The pandemic simply...

Investing in real estate is truly a full time job. Between following the law, insurance coverage, proactive property maintenance, proper tenant screening, marketing, and avoiding vacancies, we understand that landlords in Chicago have a lot on their plates. That’s why the team at GC Realty & Development wanted to put together this guide on the basics of keeping your investment property secured for your financial success.The Ch...

Landlords & Property Managers often highlight the importance of applicant screening when renting out your property. It is seen as the key to minimizing your risk when leasing to a new tenant. However, the current way most Landlords screen applicants for their rentals is flawed. In the past two years I have talked to dozens of Chicago landlords that have fallen victim to these scams. We even fell victim back to back on these sca...

Wondering about the direction of the real estate market? Dive into a recent talk with lender Chris Puleo and Mark Ainley from GC Realty & Development.In the video, Chris Puleo asks important questions for investors today. Mark Ainley, a real estate expert, shares insights from years of experience and understanding market trends.Whether you're new to investing or experienced, this conversation gives practical advice and a look at...

Mistakes will be made. That’s just a fact of being a business owner, real estate investor, or even both. No matter how careful you are, you’ll make a multitude of mistakes over the years. Some mistakes will be larger than others; some will barely register on your oh-shit-meter. But some mistakes will be so bad that you may never share them out of pure embarrassment. This is one of those pure embarrassment stories. I&rsq...