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Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast
Tim and I were back for week 26 of Chicago Landlord Secrets after doing last week’s episode in person at The Underground.
This week we covered three things Chicago landlords should be paying attention to right now: the Chicago school board and property taxes, the next mayoral race, and the fall maintenance items that need to be handled before the weather changes.
We also talked about 311 alerts, leasing pressure before the season slows down, and why maintenance communication can make or break an owner’s experience.
Chicago School Board
The first big topic was the Chicago school board and how it connects back to property taxes.
Tim brought up a story about CPS being over budget and hoping the state helps cover the gap. The part that matters for property owners is that the school board controls a major part of the property tax conversation.
A lot of landlords only think about the assessor or the county when property taxes go up. But the school board budget also feeds into the tax burden that gets spread across property owners.
That is why the school board election matters.
Tim pointed out that the current board is partly elected and partly appointed by the mayor, but the next election will make the entire board elected. For landlords, that means this is not a small political race to ignore.
You can care about good schools and still want financial discipline.
Property owners need to research who is running in their district, what their budget priorities are, and how they plan to balance school needs with the reality that property taxes are already crushing many owners and renters.
Next Mayor
We also talked about the next mayoral race and how much local politics matter for landlords.
Mark brought up Alexi Giannoulias announcing his run and mentioned that his work as Secretary of State has improved the DMV experience. Tim pushed back a little, saying some of those improvements may have started because of COVID appointment systems, but also gave credit for keeping what works.
That was the bigger point.
Chicago needs leaders who keep systems that work and fix the ones that do not.
Whether it is the DMV, CPS, property taxes, 311, inspections, or landlord-tenant laws, landlords feel the impact when city systems are slow, expensive, or poorly managed.
The mayoral race matters because housing policy, tenant laws, public safety, school budgets, and business regulation all affect whether owners keep investing in Chicago.
Landlords should not wait until Election Day to start paying attention.
Fall Maintenance
Even though it is still hot, fall maintenance is already here.
We talked about furnace cleanings, gutter cleaning, tree branches, downspouts, and storm preparation.
Furnace cleaning needs to get on the calendar before everyone calls at once. If you wait until the first cold snap, you are competing with every other landlord who waited too long.
Gutters also need a property-by-property approach. Some buildings may only need one cleaning a year. Others have trees hanging over the roof and need more attention.
The storms this year made that more important.
Branches over the roof can cause damage, create insurance issues, and become a much bigger emergency if you wait until they fall. Downspouts matter too. If water is dumping next to the foundation, you are inviting basement and crawl space problems.
We also talked about 311 alerts and why they can help landlords. Sometimes tenants do not call you first. Neighbors may report tall grass, tree damage, downed lines, or other property issues through 311. Having line of sight on those reports gives you a chance to respond before fines or bigger problems show up.
Maintenance is not just about fixing what breaks. It is about seeing problems early, communicating clearly, and helping owners understand why the work matters.
Questions We Answer in This Episode
Q: Why should landlords care about the Chicago school board?
A: Because school budgets affect property taxes, and property taxes directly affect rental property costs.
Q: What should landlords watch in the next mayoral race?
A: Housing policy, property taxes, public safety, city services, and whether candidates understand how regulations affect small landlords.
Q: When should landlords start fall maintenance?
A: Before the first cold snap. Furnace cleanings, gutter checks, tree trimming, and drainage issues should be handled early.
Q: Are 311 alerts useful for landlords?
A: Yes. They can give landlords visibility into complaints or issues tenants may not report directly.
Q: Why do maintenance costs create tension with owners?
A: Often because the invoice does not explain the full scope. Better communication and transparency help owners understand what they are paying for.
Show Notes and Timestamps
00:24 Welcome back to Chicago Landlord Secrets
01:23 Summer Soiree and supporting MBOA
04:12 Chicago school board, CPS budget issues, and property taxes
06:29 Why the school board election matters for property owners
07:03 School board reform and investor voices
08:28 Alexi Giannoulias and the next mayoral race
12:04 Property Sentinel, 311 alerts, and landlord visibility
15:53 Leasing push before the season slows down
31:51 Fall maintenance and furnace cleaning
32:08 Gutters, trees, downspouts, and storm preparation
Key Takeaways for Chicago Landlords
The Chicago school board election matters because school budgets affect property taxes.
Landlords should research school board candidates before November.
The next mayor will have a major impact on housing policy and landlord regulation.
311 alerts can help landlords catch issues before they become fines.
Fall maintenance should start before the first cold snap.
Furnace cleanings, gutters, tree branches, and downspouts need attention now.
Maintenance communication matters because owners need to understand the real scope and cost.
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
