Chicago Property Management Blog

Being a property management company owner for over 20 years and being accessible as co-host of the Straight Up Chicago Investor Podcast, I get calls every day from landlords.Most of them aren't calling because everything is going great.They call because something finally broke. A resident who keeps paying late. A repair that ate half their week. A turnover that dragged on longer than it should have. The property is still cash flowin...

A few times a month I get some version of this question from a Straight Up Chicago Investor Podcast listener or from an owner we manage for: "Mark, I have a basement I think could be a legal unit. What is the minimum ceiling height in Chicago?" It is one of the most common questions we hear when investors start thinking about legalizing an existing garden unit or carving out a new one to boost income on a building they already...

As the co-host of Straight Up Chicago Investor and as a partner at GC Realty where we manage roughly 1,500 units across Chicagoland, I get asked the same question almost every week. Should I buy a 2 unit, a 3 unit, or a 4 unit?Almost every new investor asking that question is after the same thing. They want to house hack. Live in one unit, rent the others, let the tenants pay down the mortgage while they build equity, and then either re...

At GC Realty and Development, we focus exclusively on traditional long-term property management. We do not manage short-term rentals. But we are paying close attention to what is happening in the short-term rental space across Kane and DuPage counties, because it is directly affecting the decisions property owners are making right now. We are seeing a clear and growing trend: owners who have been operating on platforms like Airbnb and V...

I have been doing this long enough to know what happens when a landlord gets desperate.They have a vacant unit. Days are ticking by. No rent coming in. Showings to coordinate. Questions piling up. And slowly, the pressure builds until they start making decisions they never would have made in month one.That is the moment I worry about the most. Not the vacancy itself. The decisions that vacancy pressure creates.I have seen it happen more...

A lot of landlords tell themselves the same thing for too long."I can handle it."And to be fair, a lot of them can. They can answer inquiries, coordinate a repair, collect rent, post the listing, show the unit after work, and deal with one late payment, one turnover, or one resident issue at a time.That is not usually the real question.The real question is whether doing it yourself is still the smartest use of your time, energ...

If you're a Chicago landlord trying to figure out how to scale a rental portfolio without losing your mind, this episode is for you. Mark Ainley has been in the trenches of Chicago real estate since 2003. He grew up in Addison, started a company out of a smelly moldy office in West Chicago, and built one of the most recognizable property management and investment operations in the region. He manages around 1,500 tenants at any given...

Most real estate investors spend a lot of time thinking about market conditions, interest rates, rent growth, and renovation costs. They spend far less time thinking about the person or company they hand their property over to once the deal closes. That is a problem. Because across Chicago and its suburbs, in courtrooms and in federal indictments, there is a long and well-documented record of property managers who did not just underperf...

When investors interview property managers in Chicago, the conversation almost always covers the same ground. What are your fees? How do you handle maintenance? How quickly do you respond to tenants? Those are fair questions. But there is one question that almost never gets asked and it might be the most important one when it comes to protecting your investment.What insurance does your property management company carry?The right answer ...

If you’re an Illinois landlord who’s been telling yourself, “At least I’m not in Chicago,” I’ve got bad news. This week Tim and I dug into a new statewide law that reaches straight past city lines and into every county, every suburb, and every “I thought I was safe” rental strategy. Then we pivoted into two things that seem small until they hit your wallet: landscaping season and the quiet...