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...
Chicago Property Management Blog
From One Unit to Many: Scaling a Rental Portfolio the in Chicago
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...
How to Deal with Bed Bugs in Your Chicago Rental Property
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...
Why Chicago is Still One of the Best Cities to Own Rental Property in 2025
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...
How to Build Long-Term Wealth as a Landlord in Chicago
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...
WHAT CHICAGO PROPERTY MANAGER HAS THE BEST REVIEWS?
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...
From the House Hacking On The Couch to 1,400 Doors: Lessons from Mark Ainley
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...
Section 8 Success in Chicago: A Landlord's Guide to Navigating Opportunity and Compliance
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...
From Rookie Mistakes to Real Estate Wins: One Chicago Landlord's Wake-Up Call
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...
Tenant Placement Services in Chicago: How to Find the Right Tenant
If you’re a Chicago landlord who thinks tenant placement is just putting an ad on Zillow and picking the first person who has cash in hand — you’re setting yourself up for a costly mistake.Over the last 23 years we have made many mistakes in this department and we want to make sure others do not. In cities like Phoenix or Columbus, maybe that works. But Chicago? We’ve got:The Just Housing Amendment - Change...
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