Chicago Property Management Blog

Tim and I had to rearrange schedules this week, but we kept the streak alive for week 25 of Chicago Landlord Secrets.This episode started with two lawsuits landlords should pay attention to. The first is tied to the Northwest Side Housing Preservation Ordinance in Logan Square and nearby neighborhoods. The second involves GreyStar being sued again, this time over alleged Section 8 voucher discrimination after secret shopping calls.We al...

I recently got to jump back on with the Chicago Housing Authority for their 2026 Owner Symposium webinar series to talk about something every housing provider thinks they already have handled: the lease. When I told a few people I was doing a whole session on building a lease, the reaction was pretty much, "Everybody uses the same lease. What is there to talk about?"On the surface, sure. Most of us pull from the same base temp...

The most common question we get from investors is some version of the same thing. What should I buy? Single family homes, a condo or townhouse, or a small multi family building? Everyone has an opinion, and most of those opinions are built on a gut feel or one deal that went well or badly a few years back.There are a lot of factors that go into that decision. Financing, price per door, cash flow, how much work the property needs, and ho...

Most of the conversations we have about new laws on Straight Up Chicago Investor or Chicago Landlord Secrets are not positive for Chicago investors. For once, this one is not horrible. I never used to see this as an issue, but in recent years, with insurance standards going up right along with pricing, I have watched investors and Homeowners Associations (HOAs) really get screwed because the notice window was so shor...

We have managed over 5,000 tenants across the last 23 years, and in that time we have heard just about every threat and excuse for why a tenant isn't paying rent. Almost always, they try to make it our fault. The truth is simpler than that. There are only a few real scenarios where a tenant can legally withhold rent in Chicago, and each one comes with specific rules about what the tenant has to do first. Get those steps wrong and it...

Ever since that HUD memo leaked over Memorial Day weekend, I have been getting the same question from owners and operators all over Chicago. Can we finally start charging pet rent on emotional support animals now?I understand why people are asking. The headlines made it sound like the rules flipped overnight. So here is the straight answer for anyone renting in Illinois. No, you still cannot, and the reason has almost nothing to do with...

Hiring a property management company is a big decision. Whether you're purchasing your first investment property, transitioning away from self-management, or changing property managers, you want to know exactly what happens after signing the management agreement.At GC Realty Residential, onboarding isn't simply paperwork. It's a structured process designed to make your transition as smooth as possible while setting your inve...

Back in June we put together our first five months of 2026 leasing results. The plan all along was to keep reporting as the season moved, so now that the books are closed on the first half of the year, here is the full six month picture, January through June 2026.The first half of the year tells you almost everything about how a leasing season is shaping up. January and February are the slow grind. March flips the switch. April and May ...

Tim finally got his hands on the first full draft of Mayor Johnson’s Protecting Renters Ordinance, so this week we went past the headlines and into the actual details being discussed.Some parts of the proposal surprised me. There are actual tenant responsibilities and consequences for blocking lawful access. But there are also new fee limits, longer notice requirements, and relocation payments that could completely change how Chic...

Recently, my team and I have been getting a steady stream of property management inquiries from Chicago investors, both in the city and out in suburban Cook County, who all have some version of the same problem. They have an eviction that has been going on forever. And these are not owners sitting on their hands. They have been aggressive at every step, doing what they are supposed to do, and the case still will not move. After hearing ...