Chicago Property Management Blog

Short-term rentals have been a moving target in the Village of Fox Lake for years, and the latest proposal on the table suggests they're about to get harder to operate, not easier. If you own a property here and have been weighing whether to run it as a short-term rental (STR), it's worth understanding where the rules started, where they may be headed, and why that uncertainty matters for your investment.The Original LimitFox La...

Recently on the Straight Up Chicago Investor podcast, we had Jason Wagner from Greystone Realty on to break down the current state of the Chicago market for investors. Jason knows this city cold, and one of the things he highlighted really stuck with me: rent growth, and specifically how uneven it has been from one neighborhood to the next. Want to watch the full episode? Check it out here.Some pockets of Chicago are posting rent growth...

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 ...