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Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast
Tim and I were joking right away because you always have to smile at the beginning for the thumbnail, and I’ve caught both of us making some ridiculous faces over the last few months. But we’re live, and we’re still running this weekly. We’re about three and a half months in now, which honestly makes me proud because most people talk about consistency and never actually do it.
This week we bounced between a few different lanes, and somehow they all tie back to the same thing: housing rules keep changing, Section 8 keeps being a headache for both landlords and tenants, and if you want fewer emergencies, spring is the time to get ahead of the boring maintenance before the expensive stuff shows up.
What we talked about in this episode
New York froze evictions because it was too hot
Tim sent me a post about New York freezing evictions due to heat. And when we say eviction freeze, we’re talking about the sheriff actually coming out and doing the lockout. Chicago has the winter version when it’s too cold. But too hot was a new one.
The record high they hit was 97. The part that made it feel even crazier is there’s a good chance some of those units have window AC or no AC at all. And it made me think about how weird Chicago is in spring. If Chicago suddenly hits 95 while boilers are still legally required to be operable, you can end up with overheating and boiler issues at the worst time.
Section 8 fraud headlines and why I don’t think CHA can operationalize it
We talked about the crackdown headlines around Section 8 fraud, specifically underreporting income and unreported household members living in the unit. The examples were basically:
A voucher holder paying very low rent while carrying expensive car payments
People living in the home who should be reported because their income affects the voucher calculation
Grandkids or family members living there but not counted, and not reported on purpose
My honest reaction was I don’t see how CHA has the manpower or willpower to pull this off consistently. We can’t even get CHA to run basic operations smoothly, and I shared a story I heard about a CHA tenant passing away and nobody knowing for months. If they can’t track basic tenant status reliably, how are they going to track who is actually living in the home?
A real nightmare scenario: CHA pulled back $27,000
I shared one of the worst CHA moments we’ve dealt with.
CHA pays out on the 1st and 15th. All of a sudden, on a payout, they pulled back around $27,000. Their reasoning was they determined the voucher holder passed away 17 months earlier and they were clawing back all the payments since then.
The daughter had effectively taken over, signed things, and the unit was never vacant, so nobody was treating it like an abandonment situation. We even had a lease renewal in that time.
We fought it, but we still ended up losing a big portion of the money. And that turned into a separate hard conversation with our client because from the owner’s perspective it feels like someone has to be accountable, but from our perspective it’s hard to prevent something like that when the unit is occupied and the program continues to recertify.
This is exactly why landlords get frustrated with CHA. It’s not that the tenants are automatically the problem. The program behavior and the clawback risk is the problem.
Section 8 has real pros, but the program is brutal for everyone
We talked through the pros that people forget:
Longer tenancies
More predictability in the sense that a Section 8 tenant is not just disappearing overnight
But the process is so slow and difficult that it’s not good for tenants either. Tim brought up that CHA is being sued by a tenant because it took nearly 18 months to let her move, and the reason she was trying to move was to escape an abusive situation. That’s not a landlord problem, that’s a program problem.
We also discussed why we don’t do pre-leasing on heavy Section 8 buildings. A market tenant says they are leaving in 60 days and they are gone. Section 8 tenants can pass inspections, have approvals fall apart, fail a second inspection, restart paperwork, give up, and then decide to renew with you anyway. You cannot assume they are out until they are physically out.
Tim shared how they measure vacancy timelines four ways because the move-out and move-in mix changes everything:
Market out to market in
Section 8 out to market in
Market out to Section 8 in
Section 8 out to Section 8 in
And Section 8 out to Section 8 in is their longest vacancy window, around 89 days.
We also talked about using that chaos as opportunity. Sometimes if their move falls apart, you can renew them by addressing something they were unhappy about, like replacing an older appliance, and locking in another lease.
DuPage crime rankings and why the story is less dramatic than people expect
We jumped into the DuPage County crime analysis and had some fun with it.
Tim asked me to guess the safest DuPage town. My first thought was Naperville, but we clarified something a lot of people don’t realize: most of Naperville is in Will County. Naperville ranked around 15th on the list.
The top three safest towns based on the data I pulled were:
Warrenville
Burr Ridge
Bartlett
I also looked at “most improved” over a five-year average. Addison showed as the most improved, which made me happy because that’s where I grew up. Wheaton was also one of the most improved.
Then we admitted the truth. DuPage is so safe compared to national averages that the differences can feel less shocking than a Chicago crime ranking would. But the angle Tim and I both like is tracking change over time. If crime drops consistently in certain areas, does that correlate with faster appreciation later? That’s the next research project.
A quick note on schools: DuPage high school ranking snapshot
I shared another dataset I pulled, top DuPage high schools based on graduation rates and college continuation type metrics.
Wheaton Warrenville South ranked #1
Naperville Central ranked #2
Lake Park ranked #3
Spring landlord checklist: do the boring stuff now
We closed with practical reminders and preventative maintenance, because this is where landlords either spend a little now or spend a lot later.
Tim’s spring priorities:
Annual gutter cleanings because clogged gutters can cause interior leaks
Dryer vent cleaning for fire safety
My add-ons:
Chicago heat rule reminder: heat has to be operable through June 1 in Chicago
Water spigots: turn on, test, or secure them depending on how you manage them
AC tune-ups and compatibility issues: older AC units may not match newer furnaces and vice versa
Freon reality: older units using older refrigerant are getting expensive fast per pound
Repair vs replace: if your AC is 16 years old, stop putting money into Freon
Pest prevention: mice and ants ramp up in spring, and blocking holes matters
Tim also dropped a wild mouse stat that sticks in your brain: if you start with two mice and let it go, it can explode into a massive problem in a year. The real point is don’t let it start. Block entry points and get ahead of it before tenants are living with it.
Questions We Answer in This Episode
Q: Why would New York freeze evictions because it’s hot?
A: The freeze applies to the sheriff lockout process. New York hit 97, and the idea is that extreme conditions can trigger temporary pauses. We discussed how unusual it is compared to the more common cold-weather freeze.
Q: Can CHA realistically crack down on fraud and unreported household members?
A: I’m skeptical. CHA struggles with basic tracking and operations, so the manpower and consistency needed for deeper fraud checks feels unlikely.
Q: What happens if CHA claws back payments after a tenant passes away?
A: We had a scenario where CHA pulled back about $27,000 after claiming the tenant passed away 17 months earlier. We fought it and still lost a portion. It becomes a painful owner conversation and it’s a reminder of program risk.
Q: Why don’t you pre-lease Section 8 units the same way as market units?
A: Because move-out timing is unpredictable. Approval and inspections can fall apart late, and tenants can end up staying or renewing after trying to move.
Q: What spring maintenance prevents the most expensive problems?
A: Gutters, dryer vents, AC prep, and pest prevention. Those are boring tasks that stop bigger leaks, fires, breakdowns, and infestations.
Show Notes and Timestamps
00:00 We’re live and the weekly streak continues
01:00 New York freezing evictions because of heat and why that’s wild
03:00 Section 8 fraud headline and why manpower is the real problem
06:00 CHA tenant passed away story and program tracking issues
09:00 The $27,000 clawback and why landlords hate program uncertainty
14:00 Section 8 pros, longer tenancy, but the move process is brutal
17:00 Why we don’t pre-lease Section 8 move-outs
20:00 Measuring vacancy timelines by market vs Section 8 combinations
23:00 DuPage crime rankings and why Naperville isn’t fully DuPage
26:00 Top safest towns and most improved crime trends
30:00 DuPage high school ranking snapshot and what metrics we used
33:00 Build Act update timing and why it likely won’t move immediately
37:00 Spring maintenance checklist: gutters and dryer vents
40:00 AC compatibility and Freon cost reality
43:00 Pest prevention and why mice multiply fast
Key Takeaways for Chicago landlords and investors
Eviction freezes can expand into new territory, and extreme weather rules are becoming more common in tenant-friendly markets.
CHA fraud crackdowns sound good in headlines, but operational reality is the bottleneck.
CHA clawbacks are a real financial risk, and even good-faith landlords can get hit hard.
Section 8 tenancy can be longer and more stable, but move-outs and approvals are unpredictable, so plan vacancy conservatively.
DuPage crime rankings are less dramatic than Chicago, but trend data over time may be a better investment signal.
Spring is the season to prevent big problems: gutters, dryer vents, AC planning, and pests.
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
