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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 three things landlords should be watching right now: Cook County property tax bills, where to invest in Chicagoland, and winter prep before the first cold snap hits.
We also talked about tornado sirens, Bears stadium speculation, tax appeals, furnace maintenance, boiler planning, and why landlords need to communicate with tenants before winter problems start.
Cook County Property Taxes
The second installment Cook County property tax bills are finally coming out, and the due date discussed in the episode was October 1.
That matters because landlords need to stop treating taxes like a surprise. In Cook County especially, the bill can jump enough to change the entire investment.
Tim looked up his own house during the episode and saw his taxes went up about $600. That kind of increase is becoming normal, and it is one of the biggest reasons rents keep rising.
Taxes and insurance are not side issues. They are two of the biggest pressures on rental pricing.
We also talked about how investors should review the property characteristics on the assessor’s website. Make sure the county is not taxing you for a garage, pool, patio, or second unit that does not exist anymore.
If you are buying, do not just trust the current tax bill. Check exemptions. If the seller has a senior freeze, senior exemption, or homestead exemption, those may fall off after closing.
A $4,000 tax bill can become $7,000 or $8,000 once the property reassesses.
That can destroy a pro forma if you did not plan for it.
Where To Invest
Tim flipped the game on me this week and asked where I would rather invest or manage.
The first question was Bears-related: if you owned property in both Hammond and Arlington Heights, where would a Bears stadium help landlords more?
My answer was Hammond.
Arlington Heights already has more restrictions and a more established market. Hammond and the surrounding areas may have more room for new opportunity, fewer restrictions, and more upside if the Bears ever actually land near the Indiana border.
Then we got into counties, Chicago, and suburbs.
For Will County versus DuPage County, I said Will County if I am dealing with evictions, but DuPage County for a long-term hold.
Will County is more efficient in court. DuPage is a more conservative long-term investment with strong assets and consistency.
For Chicago proper versus Cook County suburbs, I leaned Chicago because the city can sometimes be easier to operate in than suburbs with higher taxes, rental licenses, inspections, and local rules.
But when comparing Chicago to DuPage, I still take DuPage for the long-term strength of the asset.
We also talked about specific suburbs:
Edison Park over Lake View or Lincoln Park for long-term rental opportunity
St. Charles over Wheaton for long-term rent appreciation
Roselle over Mount Prospect because of fewer rental restrictions and lower tax friction
Elmhurst over Schaumburg if you can find the right rental
Aurora over Addison for newer rental housing stock in the right pockets
West Chicago over Bolingbrook for value and limited rental supply
Naperville for long-term appreciation, but Aurora can be a better value if you are in the right school district
The point is simple: where you invest depends on your goal.
Some areas are better for appreciation. Some are better for cash flow. Some are easier to manage. Some look good on paper but become painful because of taxes, inspections, or village rules.
Winter Prep
Even though it is still warm, landlords need to start winter prep now.
In Chicago, September 15 is the date we use across our portfolio for heating systems to be ready. That means boilers, furnaces, and heat-related issues need attention before cold weather arrives.
If you wait until the first freeze, you are no longer doing maintenance. You are handling an emergency.
Tim’s biggest advice was to schedule furnace cleanings now. Spending $100 or a couple hundred dollars on service can save thousands later.
We also talked about boilers. Boilers are not something you simply turn on and forget. They need to be serviced, drained, checked, and maintained. A boiler replacement can easily become a $20,000 to $30,000 problem, so preventative maintenance matters.
The same goes for furnace and AC compatibility. A landlord may think they have a $3,500 replacement issue, then find out the new AC is not compatible with the old furnace or the new furnace is not compatible with the old condenser. Suddenly, the problem is $6,000 or $7,000.
This is why reserves matter.
We also talked about tenant communication. Before winter, landlords should remind tenants to keep heat on if they leave town, drip water lines during extreme cold, and report issues early.
A lot of winter emergencies are not just equipment issues. They are communication issues.
Questions We Answer in This Episode
Q: When are Cook County property tax bills due?
A: In this episode, we discussed the second installment being due October 1.
Q: What should landlords check on their tax bill?
A: Check property characteristics, exemptions, and comparable properties to make sure the tax bill is realistic.
Q: Why can a tax bill jump after purchase?
A: Exemptions may fall off, improvements may get reassessed, or the county may catch up to changes made before the sale.
Q: Where would a Bears stadium create more landlord upside?
A: Mark said Hammond may create more upside than Arlington Heights because it has more room for growth and fewer existing restrictions.
Q: When should landlords start winter prep?
A: Before September 15. Furnace service, boiler planning, and tenant communication should start before the first cold night.
Show Notes and Timestamps
00:19 Welcome back to Chicago Landlord Secrets
00:38 Storms, tornado sirens, and weather concerns
03:13 Cook County property tax bills and October 1 due date
07:20 Why taxes and insurance keep pushing rents higher
10:32 How to contest property taxes and check property characteristics
12:46 Why buyers need to review tax exemptions before closing
15:20 Where Mark would invest and Bears stadium speculation
17:02 Will County vs DuPage County for investors
19:07 City neighborhoods and western suburb investment picks
24:35 Winter prep, furnace cleanings, boilers, and tenant reminders
Key Takeaways for Chicago Landlords
Cook County tax bills need to be reviewed carefully, not just paid blindly.
Investors should check exemptions before trusting a property’s current tax bill.
Property characteristics on the assessor site can reveal costly errors.
Hammond may have more upside than Arlington Heights if the Bears stadium ever moves there.
DuPage is a stronger long-term hold, while Will County can be more landlord-friendly in court.
The right suburb depends on taxes, rental rules, schools, inventory, and appreciation potential.
Furnace cleanings and boiler service should happen before the first cold snap.
Landlords need reserves for winter repairs and major system replacements.
Tenant communication before winter can prevent expensive emergencies.
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.
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
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