Vendor Portal
Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast
Chicago property manager, investor, and real estate entrepreneur Mark Ainley has seen nearly every twist this business can throw at you. From house-hacking roommates in his condo to managing over 7,000 units across the city and suburbs, Ainley’s career spans 20+ years of leases, evictions, flips, and industrial deals. His lessons today are as practical as they are battle-tested.
Let’s break down some of the best insights from Mark's journey that every Chicago real estate investor should know in 2025.
Key Advice and Insights from Mark Ainley
How a Couch and a Couple of Roommates Sparked a Real Estate Career
Mark’s first investment wasn’t a deal, it was survival. He rented out both bedrooms of his first condo and crashed on the couch. When he realized he was up a few hundred bucks a month, the light bulb went off. From that point forward, he chased deals, some smart, others full of mistakes, but every one taught him something that would eventually shape GC Realty & Development.
The Tenant Screening Mistake That Nearly Killed His First Rental
Mark’s first “real” rental experience started like many do: with a bad tenant and no system. He ran a newspaper ad, took the first sob story, accepted a partial security deposit, and within months was filing eviction paperwork. Lesson learned: sad stories don’t pay rent.
A Chicago Property Manager’s Screening Rulebook
Fast-forward to today, Mark now swears by his tenant screening matrix, a 13-point system that removes emotions from decisions. Each applicant is rated on credit, income, rental history, and other risk factors, landing them in one of three categories: approved, high risk (with conditions), or denied. It’s consistent, fair, and legally defensible, especially in a city like Chicago where tenant rights are front and center.
"Don’t Let the Tenant Move Out", Why Turnovers Are a Landlord’s Real Enemy
One of the biggest cash flow killers? Vacancy. For every one interaction GC Realty has with a two-flat in Lincoln Park, they’re interacting 9.5 times with a similar property in South Shore. That means more repairs, more complaints, more headaches. Multiply that across a portfolio and it’s clear why avoiding turnover is one of the smartest plays in the book.
Buy Your Time Back with Property Management
Hiring a property manager in Chicago isn’t just about maintenance or leasing, it’s about buying back your life. Mark breaks it down: in a non-turnover year, you’re spending 20 hours on one property. In a turnover year? 60–80 hours. Self-managing might look cheaper on paper, but what’s your time worth?
👉 Use the Management Quote Estimator Tool to find out if you can afford to get your time back.
The Real Cost of C-Class Investing
Between 2008 and 2018, Mark and his team did nearly 500 BRRRRs in C and D-class neighborhoods. On paper, those deals promised 14%–18% returns. In reality? After evictions, repairs, and real turnover costs, the return was closer to 7.8%. Opportunity cost reared its head, and in hindsight, he admits: “I wish I would’ve focused on A and B class neighborhoods from day one.”
Why Industrial Real Estate Is the Most Underrated Play in 2025
Forget retail. Forget office space. Mark’s bullish on industrial buildings, especially vintage properties under 50,000 square feet. Why? You can still buy them under $100/sqft in the Chicago area, they’re nearly impossible to build today due to code and zoning, and demand is skyrocketing. These warehouses now house everything from plumbing shops to online fitness businesses to feeder companies for massive distribution centers. With Chicago’s industrial vacancy rate hovering near 2%, it’s one of the few sectors where supply-demand imbalance still favors landlords.
Q&A: What Every Chicago Landlord Should Know
Q: How do you screen tenants fairly in C-class neighborhoods where standards like 700+ credit scores aren’t realistic?
A: Lowering your criteria doesn’t mean eliminating standards. Mark’s matrix approach allows flexibility across asset classes while still protecting the owner. For example, a high-risk applicant may be approved with extra deposit or prepaid rent, clear, consistent, and compliant.
Q: What’s the danger of ignoring Fair Housing risks?
A: In Chicago, once a Fair Housing claim is filed, you’re guilty until proven innocent. Even if your intent is fair, you’ll spend time, money, and legal resources proving it. Avoid vague criteria or inconsistent decisions, it’s a liability you can’t afford.
Q: Should I hire a Chicago property manager or self-manage?
A: Mark puts it bluntly: you can self-manage cheaper, but not if you value your time. Between handling maintenance, turnovers, leasing, and legal compliance, the hours add up. When you scale, or when your rent increases enough to create margin, hand it off. Let your portfolio grow while you stop playing manager.
Q: What if my manager is incentivized to create turnover because of lease-up fees?
A: Great question, and it’s why Mark built a system where his team is disincentivized to lose tenants. “Don’t let the tenant move out” is posted all over GC Realty’s office. Turnovers create risk, erode trust, and damage long-term ROI. A renewal is always the better win for both the landlord and the manager.
Q: What would you do differently if you started in 2025 with what you know now?
A: Mark’s answer: “I’d move faster, sell less, and stay out of the C-class grind. I would have built systems and delegated earlier. The returns in A and B neighborhoods speak for themselves, less touch, more appreciation, and more peace of mind.”
Episode Timestamps
00:00 – How a couch full of roommates sparked a real estate career
02:30 – First intentional investment (and early mistakes)
04:00 – The value of solid tenant screening
06:00 – Standards for screening across different neighborhoods
07:45 – Avoiding Fair Housing claims in Chicago
10:00 – The real cost of C and D-class rentals
13:30 – Why property management is about buying back time
17:00 – Turnovers as trust-killers in property management
20:00 – Leasing fees vs. renewals and long-term value
22:00 – Industrial real estate as a growth opportunity in 2025
26:00 – What Mark would do differently starting over
29:00 – Self-managing vs. hiring a Chicago property manager
Takeaways for Chicago Property Owners and Investors
Standardize screening with a fair, legal, and scalable system.
Avoid turnover at all costs. Lease renewals save you time, money, and tenant headaches.
Buy back your time. Property management isn’t a luxury, it’s a tool for scaling with sanity.
Invest where the effort pays off. A-class neighborhoods may have tighter margins upfront but deliver better returns with fewer issues.
Explore industrial real estate. It’s harder to build, in high demand, and less volatile than many asset types in 2025.
Connect With Mark Ainley
For more investor insights and behind-the-scenes real estate advice, follow Mark on Instagram @MarkAinleyREI or connect with him on LinkedIn. You’ll find daily lessons, property management tips, and honest takes on what’s working in Chicago real estate.
👉 Ready to get your time back? Use our Free Rent Analysis Tool to find out if professional management makes sense for your rental.
Want to hand off the headaches but keep the cash flow? Learn more about our Tenant Placement Services and how we help Chicago landlords find the right renters, without the stress.
There is a lot of information contained here if you plan on investing in real estate locally. It may seem overwhelming for those wanting to invest in the Chicago market, but it is really just a team sport. Who is on your investing team? Do you even have a team? GC Realty & Development, LLC. has a dedicated team of professionals that are willing to share their decades of experience in all facets of real estate. We handle everything from Brokerage, Leasing and Property Management. Whether you hire us or not, we are happy to provide you with our resources and expertise.
What gets me up in the morning and keeps me going twelve hours a day is the ability to add value to local area investors, in Chicago and beyond! Those who connect with me often hear me say that our goal is to bring value to everyone we come in contact with. We hope that in return, they will one day hire us for our Tenant Placement,or Property Management Services, refer us to someone they know, or leave us a review about our services. We would clearly love all three, however, we are happy whenever we get the opportunity to help!
Reach out today!
Partner / Co Host of Straight Up Chicago Investor Podcast
