Chicago Property Management Blog

The longer I do this, the more I am confident that an investor’s journey depends more and more on the resident they place in their unit over all other factors.  Even paying 20% over the market gets fixed long term.  Remember “Time Is Your Biggest Asset” as we say all the time on the Straight Up Chicago Investor Podcast. Want Better Tenants? Do This First.If you’ve ever had a tenant who paid re...

Top Landlords Are Doing This in 2025There’s a quiet shift happening in Chicago right now. It was fairly easy to become an investor between 2018 and 2021.  Interest rates were low, there was inventory, and rental rates were on the rise, even with the largest pandemic in over a century in the midst of it.During this period you have major shifts in how Chicago Realtors are conducting business with the NAR settlement, Cook County...

Between my role at GC Realty & Development & connections with investors around Straight Up Chicago Investor podcast the conversation around scaling comes up daily.  In the end everyone has 24 hours in a day but how do some investors grow faster than others?Buying the First Property Is Easy. What Comes After? That’s Where the Game Changes.Everyone remembers their first unit. Maybe it was a condo you lived in and decide...

Bed bug infestations remain one of the most frustrating and ongoing problems faced by rental property owners in Chicago. These pests not only frustrate tenants but can also threaten your investment, lead to costly extermination bills, and create legal complications if not handled immediately and properly.In this blog, we’ll explore how to identify, prevent, and manage bed bugs in your Chicago rental property while staying com...

You’re walking around your block in Albany Park. Coffee in hand. It’s not even 9 a.m. and already you’ve said good morning to two neighbors and watched three different contractors unload their tools onto porches that all look a lot like yours did five years ago. And then it hits you:This place hasn’t just changed. It’s been changing because you’ve been part of the change. You’ve seen it first ha...

In a city like Chicago, where real estate headlines swing from “doom” to “boom” faster than a Cubs losing streak, the concept of long-term wealth often gets lost in the noise. Everyone’s chasing the next big thing—off-market deals, BRRRRs, appreciation spikes—but those who actually win in this game know it’s not about the hype. It’s about consistency. And more specifically, cons...

A Real Look at Chicago's Top-Rated Property Management Companies (Through the Eyes of Another Property Manager)When you search “Best Chicago property management company” or “Top-rated property managers in Chicago,” you’ll see a handful of names. But if you’re serious about handing your building over to a professional team, don’t just trust the algorithm, look at the numbers.But this blog isn...

Let me be real with you from the start: I didn’t grow up thinking I was going to own a property management company. I wasn’t the kid dreaming of big buildings or flipping properties. I was the kid patching up his shoes to make 'em last another year, hustling side to side between divorced parents, and watching people around me struggle to get by. I didn’t grow up with much, but I grew up hungry.And that hunger taugh...

Let’s be honest: when most Chicago landlords hear "Section 8," they either lean in with interest or flinch with fear. And I get it.But what if I told you that Section 8 housing, when approached correctly or with property management professionals on your team, can provide stable income, long-term tenants, and even help improve communities.Section 8, officially called the Housing Choice Voucher Program, is federally funded...

MEET MIGUEL: A NEW LANDLORD WITH BIG DREAMS (AND NO GAME PLAN)Miguel had always wanted to invest in real estate. He did his research on Bigger Pockets and listened to local podcasts like Straight Up Chicago investor. He felt ready! So when he got a deal on a small two-flat in Chicago’s Belmont Cragin neighborhood, he jumped in.Miquel did his research on the front end about the neighborhoods pricing, average rents, proforma numbers...