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 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...

Managing rental property in Chicago offers incredible opportunities. From building long-term wealth to creating passive income, real estate investment in this dynamic city is full of promise. However, success often hinges on mastering the art and science of property management. This guide is designed to help both new and experienced landlords navigate the many aspects of self-managing property while highlighting what makes Chicago uniqu...

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...

You know, when it comes to property management in Chicago, it’s easy to fall into the mindset of "keep the place clean, safe, and make sure rent gets paid." That’s what most landlords and property managers think is enough.But let me tell you — after years of doing this and after a killer podcast we just recorded with Joey Coleman, I’m convinced that thinking is exactly what’s holding a lot of...

If you own property in Chicago, or you’re planning to invest here, congratulations! You have chosen one of the most intriguing real estate markets in the country!From tenant-friendly laws to neighborhood-by-neighborhood rent dynamics, managing rental property here requires a lot more than just collecting rent.This is the reason that more and more people — from first-time Landlords to even the most seasoned investors — ...

As a property owner, your rental property is not only a source of income but also a valuable long-term investment. However, with the rise of online platforms and digital communication, rental scams have become frequent. Scammers are increasingly targeting landlords by hijacking rental listings, impersonating property managers, or manipulating the leasing process using fake identities.In this blog, we'll explore the common red f...

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...