Vendor Portal
Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast
You know when you sit down with someone who's been through it, not just talked about it but really lived it, you end up having a way deeper conversation. You dive into topics that are meaningful and create curiosity to pull out nuggets of what the other person knows. Well, at least it might be meaningful for Chicago investors.
That’s the outcome I always get after spending time with Jared Kott of Marblestone Property Management Group.
Jared’s not just a fellow property manager, he is a friend of mine who I know would be there at 2am if I ever needed.
He’s someone who’s done the deep work, investing in the South Side of Chicago, building his business from the ground up, and learning the hard lessons that come with managing a portfolio in C and D residential class properties.
For those just finding Chicago Landlord Secrets, my name is Mark Ainley, partner at GC Realty & Development and co-host of Chicago’s #1 real estate investing podcast, Straight Up Chicago Investor. We manage over 1,400 units throughout Chicagoland and have been knee-deep in the property management game for over two decades. This blog is for landlords looking to grow smart and stress less, especially if you're managing from out of state or working with tough neighborhoods.
Built By Investors, Not Suits
Jared and I never set out to be property managers. Our stories started with investment, pain, and necessity. We were investors first, two guys who wanted to build something and do it fast. But what we found in the market was a lack of responsiveness, transparency, and reliability when it came to Property Management in Chicago.
So, like many landlords reading this, we had to build the solution ourselves. The companies we run today—GC Realty & Development and Marblestone Property Group—exist because we couldn't find anyone else to do the job right. And if you're trying to manage property in Chicago without local boots on the ground, you're going to run into the same wall we did.
The Price of Time: Why Self-Managing Isn’t Free
Not a day goes by where I talk to a Chicago real estate investor and they think they’re saving money by managing their properties themselves. They say “Property Management is too expensive” or “I can do it for cheaper”.
They are 100% right on one of those points. They can do it cheaper but self management is only less when you don’t account for what your time is worth.
So on paper, management costs money and you can do it cheaper but what are the real costs of self management? Saturdays lost, family events missed, slower growth to your portfolio, and stress accumulated. You might fix the toilet and keep the $150 service call—but you’re trading your peace of mind and most likely 3 hours of your time.
What is your time worth?
I want to take a quick detour here so you can stop and do a simple math problem.
How much did you make last year between the total of any W2 income or 1099 income at your day job?
How many hours did you work?
Let’s say you made $110,000 and worked 40 hours (40 hours a week x 52 weeks equals 2,080 hours). That would mean your hourly worth is $52.88 per hour.
Or
You made $300,000 and worked 50 hours (40 hours a week x 52 weeks equals 2,600 hours). That would mean your hourly worth is $115.38 per hour.
If you are reading this article, trust me you're someone that should be leveraging your time to get closer to your goals faster.
Out-of-State Investors: What They Mess Up In Chicago
Out-of-state investors are drawn to Chicago’s price points. But they’re often shocked by the complexity here. You need an attorney to close. You can’t collect a security deposit the way you do in Indiana or Florida. You need to contest your taxes or you’ll get eaten alive. Chicago’s RLTO and Cook County’s RTLO each bring strict rules with steep penalties.
If you’re not on top of everything you're rolling the dice in a way where the odds are stacked against you.
What It Takes to Let Go
Jared brought up some great points around what it takes for self managers to let go. Most owners who’ve self-managed have a hard time letting go. We call it the 90-day shift. During that time, we overcommunicate. We set expectations. We build trust. And what always happens is this: they start to breathe again. They take a weekend off. They spend time with their kids. And they realize they don’t have to carry it all. That’s when they ask us, “Why didn’t I do this sooner?”
Sometimes it’s not just about operations. It’s emotional. You’ve been the one handling it all—the good tenants, the problem ones, the 2 a.m. calls. It’s hard to let someone else step in. But when you do, and it’s the right team, you start to see property management as freedom—not as loss of control.
Managing C-Class and D-Class Rentals in Chicago
Managing rentals in tougher neighborhoods isn’t for amateurs. We’ve both worked in areas where you have to know every block. Where burned-out buildings sit next to homeowners trying to build something better. Where car washes operate off stolen water lines. Where tenants know the system better than you do.
The reality is, management in these neighborhoods isn’t impossible—but it is demanding. And it takes local knowledge, vendor relationships, and systems built on trial and error.
If you think you're going to walk into Englewood or South Shore and self-manage like it's Lincoln Park, you're in for a shock. These properties can cash flow great, but only if you're willing to run them tight and respond fast.
New Landlords: The Rise of Accidental Ownership
Many of today’s landlords didn’t plan on becoming one. They moved out of the city. They had a great 3% mortgage. And they couldn’t justify selling. So now they’re landlords with a huge opportunity to truly grow their net worth in a big way over the next 10 years.
We are seeing homeowners like this everyday. They might move the Chicago suburbs or even out of state. They know of the idea around investing and they know real estate creates more millionaires than any other industry and now they have the perfect scenario to get going. The hardest part in real estate investing is buying that property that makes sense to rent and anyone that bought before 2022 has the perfect storm to turn your owner occupied property into your first rental investment.
If you are someone that doesn’t want to get rid of your 3.5% interest rate let’s see what your place can rent for. Run a free rental analysis on your property here.
Trust is Earned: Cleaning Up the Mess
For both Marblestone and GC Realty & Development, new clients come to us from other Property Managers that may have dropped the ball or are not exactly in possession of good values.
Every property manager has taken over properties that were in disarray. Whether it’s tenants having too much autonomy, building violations, Chicago security deposits issues, wrong leases used, or unlicensed rentals, we’ve seen it. And we don’t judge. We fix it.
For many owners, that first call to us is filled with anxiety. But after a few months, it turns into relief—and then, trust.
It’s not uncommon for us to be the second or third company they’ve worked with. And we get it. The last guy didn’t explain the rental license. The guy before that disappeared. We’re not perfect, but we’re always reachable. And we always own the problem.
Data-Driven Decisions in Chicago Property Management
At GC Realty, we track thousands of work orders, lease renewals, tenant screening outcomes, and vendor timelines. That data fuels our decision-making. We know which ZIP codes require more maintenance. We know the average work order per unit per year.
For example, 60617—South Chicago—had nearly 3,000 work orders across 127 units in three years. That’s almost one work order per unit per month. And that’s not a guess. That’s real data from our system. It tells us where to expect appliance turnover, plumbing issues, and where preventative maintenance matters most.
We use this insight to advise our clients: where to buy, where to invest in upgrades, and where you better have strong leasing in place.
The conversation with Jared was deep and would be of interest to any Chicago Real Estate investor. Check out the video of our conversation and stay tuned for future Chicago Landlord Secrets episodes.
If there is a topic you are interested in discussing as it relates to Chicago real estate investors drop me an email and I will be sure to respond 100% of the time.
Curious if your rent is aligned with the market?
Need help finding a qualified tenant fast?
This is a lot of information you need to know if you plan to invest here in the Chicago market and it may seem overwhelming but real estate investing in Chicago is a team sport. Who is on your real estate investing team? Do you have a team? GC Realty & Development has a team of resources and we are willing to share all of our 20+ years of experience in both real estate investing and Property Management in the Chicago market. We will do this whether you hire us or not.
What gets me up in the morning and keeps me going 12+ hours a day of work is the ability to add value to Chicago real estate investors. If we connect you will here my say our goal of our company is to have value to have everyone we come in contact with and in return we hope one day you will hire us for our Tenant Placement or Property Management Services You can also refer us to someone you know that needs Tenant Placement or Property Management Services, or I will take a simple 5 Star Google review. We love the opportunity when we get all three from current and aspiring investors we get to help!
Reach out today!
Partner / Co-Host of Straight Up Chicago Investor Podcast
