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Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast
This week on Chicago Landlord Secrets, Tim and I talked about what the latest storms have done to South Side and south suburban rental properties, why landlords need to start thinking about heat before summer is even over, and which Chicago suburbs Tim would rather invest in right now.
We also got into the Bears stadium rumors, the Hammond/Wolf Lake speculation, ADUs, and how government keeps creating housing problems while landlords and tenants get blamed for the fallout.
Tornados
The south side and south suburbs got hit hard again.
Tim had several properties dealing with storm damage, including trees falling onto roofs, shingles blowing off, roof leaks that were not there before, and one property in Chicago Heights where the roof collapsed enough that the home became uninhabitable.
The hard part is not just the damage. It is the timing.
When storms hit this many properties at once, every roofer is backed up. Tim said they are calling through every roofer they know, then going beyond their normal vendor list because the usual crews are buried.
That creates tough conversations with owners.
In a normal summer, a roof leak may be addressed quickly. But when one house has a bucket under a leak and another house has a roof collapse, the roof collapse has to come first.
That is triage.
We also talked about how preventive maintenance matters before storm season. If a roof already looks like it only has a few years left, a major windstorm may be the thing that finishes it off.
The same goes for fall maintenance. It is still hot outside, but landlords need to start thinking about boilers, heating systems, gutters, trees, and downspouts now.
In Chicago, heating systems need to be ready by September 15. That means landlords should not wait until the first cold night to figure out whether the boiler works.
Boilers especially need regular service. Draining, checking, and maintaining the system can save landlords from a much larger bill later.
Bears News
We also talked about the Bears stadium situation because another press conference was expected later that day.
The problem is that landlords and investors are still waiting for real answers.
Arlington Heights still seems obvious to me, but there are still rumors around Hammond and Wolf Lake. Tim mentioned that if the Bears end up near Wolf Lake, that could create opportunity on the Illinois side too, especially around Hegewisch and the Southeast Side.
That area is already getting more attention.
A few weeks ago, we talked about Hegewisch and how more buyers are starting to look there. If you combine that with a possible Bears stadium near the border, restaurants, commercial activity, and more visibility, it could become a real speculative play.
That does not mean it is guaranteed.
A lot still has to happen.
But investors who understand the area, the pricing, and the risk may see opportunity before the broader market catches up.
We also touched on short-term and midterm rental restrictions. More suburbs are talking about bans, caps, or tighter rules around short-term rentals. Long-term rentals are not getting the same level of attention, but it is another reminder that investors need to watch local government meetings, not just the purchase price.
Chicago Suburbs To Invest
The fun part of the episode was putting Tim on the spot with suburb matchups.
I gave him two suburbs at a time and asked which one he would rather invest in or manage.
His answers were practical and based on what landlords actually care about: rent-to-price ratios, government difficulty, taxes, inspections, tenant quality, and how painful the village is to work with.
Some of the strongest takeaways:
Dolton beat Lansing and Hazel Crest because the rent-to-price ratio is stronger and the government is easier to work with.
Lansing beat Chicago Heights because it is less dysfunctional and has better appreciation potential in certain pockets.
Tinley beat Orland because Orland has rental restrictions that make it much harder to buy and rent.
Midlothian beat Chicago Heights because the tenant quality and stress level are better, even though Chicago Heights may offer cheaper pricing.
Oak Lawn beat Chicago Heights for lower-risk investors, while Chicago Heights may offer higher risk and higher return.
Dolton beat Riverdale because rents are better and the risk profile is stronger.
Riverdale beat Markham because Markham has become extremely difficult from an investor and village process standpoint.
Harvey beat Riverdale and Markham because Tim thinks the newer leadership has made progress.
Matteson beat Hazel Crest, mostly because the tax situation may be more favorable.
University Park beat Hazel Crest and Park Forest because of lower taxes, investor-friendly leadership, and possible opportunity tied to Governors State University.
Then we ended with city versus suburbs.
Tim’s answer was suburbs, especially in C and D-class areas, because the purchase prices, voucher programs, and rent-to-price ratios can make more sense than similar opportunities inside the city.
The big lesson is that suburbs cannot be lumped together.
One village can be a good investment market. The next village over can be a paperwork nightmare.
Questions We Answer in This Episode
Q: What storm issues are landlords dealing with right now?
A: Roof leaks, missing shingles, tree damage, water intrusion, and in some cases, properties becoming temporarily uninhabitable.
Q: Why are roof repairs taking longer after the storms?
A: Roofers are overwhelmed, so property managers have to prioritize the worst damage first.
Q: When should Chicago landlords have heating systems ready?
A: By September 15, especially for Chicago properties where heat requirements start coming into play.
Q: Could the Bears stadium create investment opportunity near Hegewisch?
A: Possibly. If Wolf Lake or Hammond becomes real, nearby Illinois neighborhoods could benefit from added commercial activity and attention.
Q: Which suburbs stood out for investment?
A: Dolton, Lansing, Tinley, Midlothian, Harvey, Matteson, and University Park all came up as stronger options depending on the investor’s risk tolerance.
Show Notes and Timestamps
- 00:15 Welcome back to Chicago Landlord Secrets
- 00:34 Storm damage across the South Side and south suburbs
- 01:32 Tornado touching down near Tim’s house
- 03:05 Roofers backed up after repeated storms
- 05:03 Tough owner conversations and repair triage
- 08:42 Heating systems and September 15 preparation
- 10:54 Chicago suburb investment matchup game begins
- 18:23 City versus suburbs for rental investment
- 19:24 Bears stadium press conference and Hammond rumors
- 29:05 ADUs, housing supply, and government barriers
Key Takeaways for Chicago Landlords
- Storm damage has created a real repair backlog in the south suburbs.
- Roof leaks need to be triaged when multiple homes are damaged at once.
- Preventive maintenance before storms is cheaper than emergency repairs after storms.
- Heating systems and boilers need attention before September 15.
- Bears stadium speculation could create opportunity near Hegewisch and Wolf Lake.
- Short-term rental rules are changing in many suburbs, so investors need to watch local meetings.
- Suburb selection matters as much as property selection.
- Dolton, Lansing, Tinley, Midlothian, Harvey, Matteson, and University Park all offer different risk/reward profiles.
- Markham was called out as one of the hardest investor markets because of village issues.
- In C and D-class areas, some suburbs may offer better numbers than the city.
Guest Information
Mark Ainley
Founder & Partner – GC Realty & Development
Podcast Co-Host – Straight Up Chicago Investor
Tim Harstad
Founder – Chicago Style Management
Because finding good tenants and property management shouldn’t feel like online dating.
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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,
Founder, Partner, Podcast Co-Host, and Investor
