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Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast

Let me just say this up front—if you're one of those investors thinking you need a hundred units and a fancy syndication to "make it," you’re missing the point. And in this episode, Katie and Rob Hayes make that crystal clear. They’ve built a portfolio that works for their lifestyle—not the other way around—and they’ve done it by staying local, staying focused, and staying in control. No gimmicks. No guru fluff. Just real talk about how to build wealth slowly and smartly right here in DuPage County.

I’ve known Katie and Rob for years, and what I love about their story is how intentional they are. They’re not out chasing the latest trends or stretching themselves thin across six zip codes. They’re biking neighborhoods with a map and a highlighter. They’re following up on door hangers. They’re managing their properties because it works for them. And they’re living the investor lifestyle on their terms—with fewer properties, more control, and better returns.

If you’re a landlord in the Chicago suburbs—or looking to be one—this is a must-listen. We talk about scaling without burning out, finding off-market deals the right way, turning a W2 into a real estate business, and making short-term and midterm rentals profitable even in areas people overlook. And yes, we get into how to self-manage without pulling your hair out.

Bottom line—this episode is a clinic on how to GSD and play the long game. Whether you’re just getting started or thinking about pivoting, this is 60+ minutes of practical gold from two people actually doing the work.

Learn how to grow your rental portfolio in one of Chicagoland’s most sought-after counties without overextending yourself, and discover why suburban rentals—especially in landlord-friendly Du Page—might be your next best move.

Questions We Answer in This Episode

Q: How can property managers and landlords start building a rental portfolio in DuPage County?
A: Start by defining your ideal property type and target neighborhood. Focus on A/B-class areas near transit, schools, and strong local economies. DuPage County offers lower tenant turnover, fewer municipal restrictions than Cook County, and stable appreciation.

Q: What are the pros and cons of investing in C-class properties vs. A/B-class rentals in the suburbs?
A: While C-class properties offer lower purchase prices, they often come with increased management headaches, slower appreciation, and higher turnover. A/B-class neighborhoods offer higher quality tenants, less drama, and stronger long-term returns.

Q: What’s the best way for landlords to find off-market rental properties in suburban markets? A: Use direct mail, door hangers, cold calls, and in-person neighborhood farming. Focus on distressed properties or tired landlords. Consistency and local presence help beat competition in low-inventory areas like Downers Grove.

Q: Should property owners in DuPage County consider Airbnb or midterm rentals?

A: Yes, especially in towns with local events, hospitals, or corporate offices. Short-term and midterm rentals can generate significantly more income than traditional leases, especially with furnished properties near transit hubs.

Q: How can property managers avoid burnout when self-managing suburban rental properties? A: Invest within a 10- to 15-minute radius. Build strong systems for tenant communication, maintenance, and accounting. Avoid overcommitting—know your limit and hire help or third-party managers when needed.

Q: What’s the most effective lead generation strategy for landlords looking to expand in DuPage?
A: Create a lead map and physically canvas target neighborhoods. Track your efforts. Combine this with outbound calls and follow-up systems. Locals trust consistent, visible investors more than strangers dropping postcards.

Q: How do suburban zoning laws impact Airbnb and short-term rentals?
A: Many DuPage towns are evolving in their treatment of short-term rentals. Some now require permits, others ban it. Always verify with the local government, and plan backup exit strategies like furnished midterm leases.

Q: What makes DuPage County ideal for long-term property management success?
A: DuPage has good schools, strong infrastructure, landlord-friendly governance, and low crime. All of these factors contribute to high-quality tenants, long stays, and reduced management friction.

Q: How can investors scale a portfolio intentionally without taking on unnecessary risk?
A: Focus on one area, understand the local dynamics, pay off mortgages strategically, and grow at a sustainable pace. Avoid syndications and speculative plays that don’t align with your lifestyle goals.

Q: What advice do experienced landlords have for people buying their first rental in the suburbs?

A: Start with one solid property in a location you'd live in. Save aggressively. Be patient. Learn the tenant laws and keep all documentation tight. Build your first property as a system, not just an address.

Show Notes

00:00 – Farming neighborhoods and using maps to find off-market rentals
06:28 – First profitable flip and transition into long-term rentals
13:00 – C-class properties vs. A/B-class suburban rentals
24:55 – Leaving W-2 jobs and going full-time into real estate
29:44 – Driving for dollars and door-to-door lead generation
39:17 – Scaling down: fewer properties, more control and cash flow
44:32 – How much Airbnbs make in Downers Grove vs. traditional leases
50:06 – Navigating local zoning laws for short-term rentals
53:27 – Backup plans: converting short-term rentals to long-term leases
58:55 – Advice for first-time suburban rental property investors

Takeaways for Chicago Property Managers and Landlords

You don’t need 50 doors—just a few good ones and a clear goal
Local rentals = faster response times, better tenant relationships, and higher retention
Door hangers and cold calls work—especially when done consistently
Midterm rentals are emerging as a high-cash-flow alternative to long-term leases
Zoning laws vary—know your town’s rules for Airbnbs and short-term stays
The best deals are often walking distance—start with neighborhoods you know
Fewer, better properties = more profit and less management stress
Furnishing rentals can boost income by 50–70% if done right
Set up weekly planning meetings to stay aligned on goals
Self-managing landlords need systems just as much as full-time pros

Guest Name: Katie and Rob Hayes

Guest Company: Platinum Partners Realtors

Guest Link: https://www.pprhomes.com/agent-detail/Rob-Hayes/179243/

Because finding good tenants and property management shouldn’t feel like online dating.

Dear Investor,

If you are an investor in either the city or suburbs of Chicago, I would love to speak with you about how we can help you on your real estate journey. At GC Realty & Development LLC, we help hundreds of Chicagoland real estate owners and brokers each year manage their assets with both full service property management and tenant placement services.

We understand that every investor’s goals are unique, and we love learning about each client’s individual needs. If there is an opportunity to help you buy back your time by managing your rental property or finding quality tenants, please check us out.

Best Investing,