Chicago Property Management Blog

If you’re a Chicago landlord who thinks tenant placement is just putting an ad on Zillow and picking the first person who has cash in hand — you’re setting yourself up for a costly mistake.Over the last 23 years we have made many mistakes in this department and we want to make sure others do not.  In cities like Phoenix or Columbus, maybe that works. But Chicago? We’ve got:The Just Housing Amendment - Change...

I have had the opportunity to own and manage properties in other larger and smaller cities across Chicago and the suburbs, it is just very unique when it comes to Property Management.  It isn't even just that cut and dry to say “Chicago”, because there is so much uniqueness within the 6 counties, 183 municipalities, and thousands of individual HOA’s that make up Chicago real estate.  If you’ve ever ...

Why Abandonment Isn't as Simple as It SoundsIn the world of property management, few topics generate as much confusion as abandonment. To a casual observer, it might seem straightforward: if a tenant stops paying rent and disappears, they must have abandoned the property, right?Not quite.In Illinois—and especially in Cook County and the City of Chicago—the legal definition of abandonment varies by location, and the wrong...

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...