Chicago Property Management Blog

Chicago Landlord Secrets is a live show we record each week on my personal LinkedIn and the Straight Up Chicago Investor Facebook page.  Learn here what you need to know to grow faster & smarter in the Chicago real estate market. Join live and ask questions, or reach out anytime.  We help with Tenant Placement & Property Management, are here for Chicago investor questions as well. Connect Today!The rental landscape in ...

Chicago Landlord Secrets is a live show we record each week on my personal LinkedIn and the Straight Up Chicago Investor Facebook page. Learn here what you need to know to grow faster & smarter in Chicago real estate. Join live and ask questions or reach out after anytime. Connect Today!There is a lot to break down when it comes to rental licensing in Chicago and in the over 80  suburbs.  If you want to lease your property...

Chicago Landlord Secrets is a live show we record each week on my personal LinkedIn and the Straight Up Chicago Investor Facebook page. Learn here what you need to know to grow faster & smarter in Chicago real estate. Join live and ask questions or reach out after anytime. Connect Today! I get the opportunity to talk to hundreds of Chicago investors a year and the question often comes up “Should I Accept Pets”... or...

Why Tenant Screening Matters More Than Ever in 2025I get the opportunity to talk to Chicago and suburban real estate investors everyday. I hear the pains they create for themselves by not following industry best practices, and I’ll tell you about some of those in this article. Chicago has a rental market that is no stranger to change.Tenant-friendly laws have expanded across the city and suburbs. A rise in rental application fraud...

If there is one County in Illinois that I would tell everyone is the best county to invest in real estate in, that county would be DuPage county and within DuPage County Naperville is the largest city.Naperville is one of the top-rated suburban cities in Illinois and the Midwest. The prime location is ideal for real estate investors and Landlords. Known for its nationally ranked schools, vibrant downtown, and low crime rates, Naperville...

When it comes to managing apartment buildings in Chicago, one size definitely doesn’t fit all. As both an Investor and Property Manager myself, this resonates with me. Not every investor is the right fit, even if that Property Management Company is amazing.  Whether you're a Chicago property owner looking to delegate day-to-day operations, navigate local laws or handle maintenance requests, we can help. Choosing the right...

Understanding the Need for Chicago Property ManagementOwning rental property in Chicago comes with incredible opportunities, but also challenges that are often underestimated—especially for first-time landlords or those managing from a distance.Navigating Chicago’s specific and sometimes unforgiving rental market requires not only time but also an in-depth understanding of local regulations, tenant rights, and seasonal dynam...

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...