There is still money available. There are still lenders, contractors, property managers, brokers, wholesalers, and resources to help investors execute once they find the right opportunity. But in today’s market, the hardest part is often finding the actual property.In this Straight Up Tuesday Tip, Mark Ainley and Tom Shallcross talk through three simple ways Chicago real estate investors can create more deal flow without overcompl...
Chicago Property Management Blog
How Lease Violations Are Handled in Illinois, From First Warning to Court
How Illinois landlords should document, notice, and escalate a lease violation, and what changes in Chicago and suburban Cook County before a case ever reaches court.Most lease violations I see don't start as eviction cases. They start as a late payment, a dog in a no pet unit, or a boyfriend who never seems to go home. How you handle that first moment decides a lot. Handle it cleanly and most of these get resolved with a phone call...
How to Run a Credit Check on a Tenant in Illinois
We handle close to 500 lease transactions a year across about 1,500 units in Chicagoland, and every one of them starts with screening. Credit is usually the first thing an owner asks about. It shows how an applicant handles their obligations, whether there are collections or a prior landlord judgment, and whether the rent fits on top of what they already owe each month.Pulling the report is easy. Pulling it the right way in Illinois tak...
Chicago Heating Issues, 1031s, & Update on PRO: Chicago Landlord Secrets
This week Tim and I got into some of the heating issues landlords deal with every year, especially in older Chicago buildings. We also answered a good listener question about when a 1031 exchange actually makes sense, and wrapped up with the latest PRO update from City Hall.Chicago Heating IssuesHeating season always exposes problems that were easy to ignore during the summer.One of the biggest challenges is boiler buildings.Boilers can...
Security Deposit Rules in Illinois: How Much You Can Charge and When to Return It
The security deposit is the smallest number in your lease and the one most likely to land you in court. I have been managing rentals in Chicagoland since 2003, and our team at GC Realty now oversees roughly 1,500 units across more than 100 municipalities. The pattern never changes. Owners rarely get sued over rent. They get sued over a $1,200 deposit they held a week too long or a paint charge they could not back up with a receipt.Illin...
Chicago PRO Update, Rental As A Business, & Cash Flow: Chicago Landlord Secrets
Week 37 of Chicago Landlord Secrets brought another update on Chicago’s proposed rental law changes, but once again the biggest development was that there was no final vote.Tim and I also got into a topic that comes up constantly with owners: treating a rental property like a real business. That means budgeting for maintenance, planning ahead for major repairs, and understanding that cash flow is only one way real estate creates w...
Elgin Rental License and Inspections, What Landlords Must Know
Elgin is one of the most active rental licensing towns in the western suburbs, and it doesn't leave much room for owners who learn the rules after a tenant moves in. At GC Realty we manage 30+ rental units in Elgin today, and we've taken hundreds of properties through the city's licensing and inspection process over the years.If you're converting the home you used to live in or buying your first rental in Elgin, this is ...
Illinois Flood Disclosure for Landlords in 2026 and What Actually Counts as Flooding
It rains hard in Chicago for two hours. The storm sewers can't keep up, water comes up through the floor drain in the garden unit, sits there for an hour, and goes back down. By morning the floor is damp and the tenant has a few wet boxes.Now the landlord has a question. Do I have to put that on the flood disclosure?We get versions of that question constantly from owners, realtors, and even other property managers. The Illinois floo...
What the Chicago Tenants' Rights Ordinance Actually Is (and It Applies to Investors)
With everything going on in Chicago housing provider news these days, the phrase "Chicago rights ordinance" gets tossed around constantly. But the real meaning of that name points to the 2013 Tenants' Rights Ordinance, which is a completely different animal from the RLTO and from any of the proposals being fought over right now in City Hall.I've been operating in this market since 2003, and I still watch people confuse...
Chicago Landlords Are At Risk: What The Proposed RLTO Changes Could Cost You
Chicago is about to rewrite the rules for every landlord in the city, and most owners I talk to have no idea how close it is. Two competing proposals to overhaul the Residential Landlord and Tenant Ordinance, the RLTO, have already cleared City Council committees. A full vote was on the table this week before it got pushed to later this fall. If you own rental property in Chicago, you are at risk of new fees, new paperwork, new limits o...
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