Chicago Property Management Blog

A personal note from Mark Ainley on being featured in a Progress Podio case studyThis is the operator's side of that story. (Progress Software, the company behind Podio, recently published a full case study about what we built. If you want the version written for the software side of the story, that's the link.) What follows is what it actually felt like to be on the inside of that growth.Property management has 5 core processes...

This is the third article in our DuPage County data series. Article 1, The 5 Safest DuPage County Suburbs for Real Estate Investors (FBI Data), identified the five lowest violent crime towns in the county. Article 2, Where DuPage Crime Is Falling Fastest: 5 Suburbs to Watch, identified the five towns where crime has trended down fastest over the past 5 years. This article is the full reference table. Every DuPage County municipality (an...

I brought Peter Lohman into the underground for an in person conversation, and I’ll be honest, I was pumped for two reasons.First, I haven’t sat down with many people from the property management world outside of Chicago in this kind of setting. Second, Peter has quietly built something in the industry that a lot of people talk about like it just “happened” overnight.It didn’t.We covered newsletters, commun...

I almost didn’t think we were going to record this week, but we squeezed it in. And I’m glad we did because Tim and I had a fresh download from spending three and a half days together in New Orleans at NARPM, the National Association of Residential Property Managers annual conference.This episode was a mix of what’s coming next in property management, what’s already here, and a few landlord realities that nobody ...

Owning rental property in Chicago comes with clear legal responsibilities. One of the most important is ensuring that every rental unit meets habitability standards. These laws are designed to protect tenants by requiring landlords to provide safe, livable conditions throughout the duration of a lease. Failing to meet habitability requirements can lead to tenant disputes, legal claims, and financial penalties. For property owners, ...

When investors ask us about crime in a Chicagoland market, they usually ask the wrong question first. They ask, "What's the crime rate?" The better question is, "What's the crime trend?" A town with a slightly elevated current crime rate that has been trending down for five years can be a stronger investment story than a town with a low current rate that's been creeping up. Trend tells you where the marke...

For years, real estate professionals were told to keep quiet on two of the questions buyers and investors ask most often: "How are the schools?" and "What's the crime like?" That changed in April 2026, when HUD issued new guidance clarifying that agents and brokers can lawfully share neighborhood crime data and school performance information with clients, as long as the data is presented factually, consistently, ...

There is a new housing plan moving through Springfield that every Chicago area investor should know about. It is called BUILD, and it could change how, where, and what you build across Illinois. On the Straight Up Chicago Investor Podcast, we talk a lot about how rules and laws shape your bottom line. This one is big. So I want to break it down for you here in plain words. No jargon. Just what it is, where it stands, and what it could m...

If you have spent any time working with a real estate broker in Illinois, you have probably heard some version of this exchange. The buyer asks about the neighborhood. Maybe they want to know about the schools. Maybe they want to understand the crime situation before they make one of the biggest financial decisions of their life. And the broker, trained to avoid the topic entirely, redirects them to a website and moves on. That has been...

If you’ve ever left a networking event and woke up the next morning with a sore throat and zero voice, you already know how this one starts. Tim and I were both coming off the MBA PAC event, and we were basically trying to hydrate our way back to normal. He was boiling ginger. I was just trying to sound like an adult.But even with the raspy voices, this week ended up being a really practical conversation for landlords, especially ...