Chicago Property Management Blog

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...

Here is how it used to go. You find someone living in your vacant unit. No lease. No permission. Nothing. You call the police, and nine times out of ten they tell you it is a civil matter and not something they can touch. So now you are calling your attorney, and he gives you the news you did not want to hear. Post notice, file for eviction, and get comfortable, because this could take months. I have seen it drag closer to a year in a f...

I still hear it every week. A landlord tells me they "don't do Section 8" because the tenants don't pay, don't work, or will trash the place. Then I ask if they have ever actually managed a Section 8 tenant. More often than not, the answer is no. They are repeating something they heard from another landlord, who heard it from someone else, who probably had one bad experience a decade ago. Meanwhile they are sitting...

Back in March I shared the 2025 numbers from my friends over at Property Shield, and they were ugly. Nearly 16,000 fraudulent rental listings across the Chicago metro in a single year. I told you then that this problem was not slowing down. Well, the first half of 2026 is in the books, and the data confirms exactly what we are seeing on the ground. Fraud is not backing off. On a month for month basis, it is getting worse.If you own...

GC Realty gets hundreds of inquiries every month for property management, and a large chunk of those people are stuck on the same question. Should I sell, or should I rent it out? So we spend real time with them breaking down the opportunity they already have, why Chicago is a great place to be invested, and all the ways you can make money by keeping the property as a rental. This blog is that same breakdown. If you are sitting on a ren...