Chicago Property Management Blog

Investing in a rental property in Chicago comes with a good income potential, but only if you’re strategic with your leasing approach. One of the most effective methods to maximize rental income is tiered lease agreements. These structures give tenants options based on lease term lengths while helping you to secure stable income and reduce vacancy.What Are Tiered Lease Agreements?Tiered lease agreements are a type of rental a...

The Problem Chicago Landlords Face TodayPicture yourself showing up at your vacant Chicago rental to show a prospective tenant the place to lease. When you go to put your key in the lock at the front door for some reason it doesn't go in the slot or it goes in and doesn't turn?  You ask yourself “what in the … I was just here 2 days ago, I know this key works!”Then you walk around back, and you notice ga...

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...