Chicago Property Management Blog

This week on Chicago Landlord Secrets, Tim and I talked about three things landlords should be watching right now: Cook County property tax bills, where to invest in Chicagoland, and winter prep before the first cold snap hits.We also talked about tornado sirens, Bears stadium speculation, tax appeals, furnace maintenance, boiler planning, and why landlords need to communicate with tenants before winter problems start.Cook County Proper...

Ask ten Chicago area owners what a property management company does and nine of them will say some version of collect the rent and call a plumber. I have been managing property in Chicagoland since 2003 and I still hear it on discovery calls every week.Rent collection is real work, but it is maybe two percent of the job. The actual work sits in three buckets, and almost everything a good company does for you falls into one of them. Leas...

I get this question every single week. Sometimes it comes from a brand new investor who just closed on a two flat. Sometimes it comes from a guy who has owned buildings for 30 years. The question is always the same and it always shows up with a little bit of anger behind it."Mark, the tenant has not paid me in two months. What am I allowed to do?"Here is the honest answer. You are allowed to follow the written law. That is it....

This week on Chicago Landlord Secrets, Tim and I talked about what the latest storms have done to South Side and south suburban rental properties, why landlords need to start thinking about heat before summer is even over, and which Chicago suburbs Tim would rather invest in right now.We also got into the Bears stadium rumors, the Hammond/Wolf Lake speculation, ADUs, and how government keeps creating housing problems while landlords and...

Feedspot refreshed its ranking of the best Chicago real estate podcasts on August 1, 2026, and it is a genuinely useful list. Eight shows made the cut. I want to walk through the top five, counting down from number five to number one.Full disclosure before we start. Our show, Straight Up Chicago Investor, is on this list. So rather than rank these by my own opinion, which would be worthless to you, I am using Feedspot's or...

Changing property management companies can feel overwhelming, especially if your rental property is already occupied. You’re probably worried about disrupting tenants, losing important records, or creating unnecessary delays. But if your current property manager isn’t meeting expectations, switching management teams isn't just about operational improvements. It's about reclaiming confidence in knowing your property i...

Short answer: Self-managing is cheaper on paper almost every time. A Chicagoland property manager typically costs 7–10% of collected rent, so on a $2.200/month rental you're looking at roughly $1,848–$2,640 a year. If you handle the leasing, the maintenance calls, the license renewals, and the compliance yourself, you keep that money.The catch is that the comparison only works if your time is worth $0 and your legal expo...

Feedspot just updated its list of the best Chicago real estate podcasts and Straight Up Chicago Investor came in at number one. You can see the full list right here: Best Chicago Real Estate Podcasts on Feedspot.Tom and I have been doing this show for six years now and it has never been about rankings. What actually matters is what happened on the other side of the microphone. We have watched listeners go from zero properties to their f...

Tim and I were back for week 26 of Chicago Landlord Secrets after doing last week’s episode in person at The Underground.This week we covered three things Chicago landlords should be paying attention to right now: the Chicago school board and property taxes, the next mayoral race, and the fall maintenance items that need to be handled before the weather changes.We also talked about 311 alerts, leasing pressure before the season sl...

Property management companies love talking about door count.500 doors.1,000 doors.5,000 doors.The assumption is simple: more doors must mean a bigger, stronger, and more valuable property management company.Not necessarily.A company can add hundreds of rental properties and still be difficult to scale, barely profitable, completely dependent on the owner, and almost impossible for another company to acquire.Real growth is not just addin...