Chicago Property Management Blog

For years, the rule in Chicago real estate was simple: buy low, renovate fast, flip for a quick check, move on. And that rule isn't going anywhere anytime soon. A recent fix-and-flip industry survey found that 71 percent of investors plan to buy more properties in 2026 than they did in 2025, the highest share ever recorded. Flippers are still buying. But smart investors are starting to rethink what happens next. With material c...

If you own a home with a Fannie Mae backed loan and you're planning to move out, keep the house, rent it to a tenant, and buy a new primary residence, there's a documentation rule you need to know about before you go under contract on your next home. Not sure which kind of loan you have? You can check using Fannie Mae's free Loan Lookup tool. If your current mortgage is an FHA loan, that is not the same as a Fannie Mae loan,...

Tim was out on vacation this week, so I brought in John Warren as a guest co-host for Chicago Landlord Secrets.John is the managing broker of 20 Properties and focuses on the near western suburbs, including Berwyn, Cicero, Lyons, Forest Park, and parts of Oak Park. He also owns and manages value-add rental property, so this episode got into the real day-to-day issues that come with managing apartments.We talked about lease timing, AC un...

As a property manager here in Chicago, and as someone who hosts a real estate podcast covering the local market, Section 8 comes up constantly in conversations with landlords and investors. Of the roughly 1,500 units we manage across the Chicago area, about 10% are leased to tenants using CHA vouchers, so passing inspection isn't theoretical for us. It's part of the operation every month.Section 8 inspections trip up more landlo...

I've had more than one landlord ask me some version of "what's this NSPIRE thing I keep hearing about, and do I actually need to worry about it yet?" The short answer is yes, eventually, but not tomorrow. The longer answer is worth understanding now, because the inspection your voucher units pass today isn't the inspection they'll need to pass once this fully takes effect.What NSPIRE Actually IsNSPIRE stands fo...

Over the last 20+ years, I've bought, renovated, and managed hundreds of rental properties across Chicago, and a huge chunk of that portfolio, both my own and the ones GC Realty manages for other investors, has run through the Chicago Housing Authority at some point. At any given time we've got hundreds of CHA units under management, year after year, so I've seen this program play out in just about every way it can.I get ask...

In July 2026, one of the biggest federal housing bills in decades quietly became law. There was no big signing ceremony. President Trump refused to sign it in protest over an unrelated voter ID measure, and it became law automatically after he chose not to veto it either.You have probably not heard much about it, and there is a reason for that. It did not pass with a headline moment, so it never really registered with most people the wa...

If this is your first rental property, the term "property management service" probably sounds bigger and vaguer than it needs to be. Owners picture someone who collects rent and fixes a leaky faucet. That is part of it, but it is a small part. After more than two decades managing rental property across Chicagoland, I can tell you the job is a lot more involved than most first time landlords expect, and knowing what it actually...

If you read my January piece on how to actually pull your Section 8 number in Cook County, this one is different. That article was about the mechanics, how to read the chart, subtract for utilities, and check your voucher size. This one is about the money itself, what happened to Cook County payment standards over the last two years, why the number swung the way it did, and what that means for your 2026 numbers specifically.Here is the ...

HB 3564, the amendment to the Illinois Landlord and Tenant Act adding rental fee transparency and limitations provisions, was signed into law by Governor Pritzker on June 26, 2026. You can read the full text and bill status of HB 3564 on the Illinois General Assembly website if you want to go straight to the source. The Chicagoland real estate industry now has to dissect what changes must be made to the current way of doing business. Th...