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Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast
Chicago landlords can ignore a lot of things, but sewer backups and program chaos aren’t on that list. This week Tim and I covered three topics that keep showing up in real conversations with owners: what causes Chicago basement flooding and what you can do to reduce the damage, what the new ADU map really means in practice, and why CHA is still one of the most frustrating housing programs to work with even when the tenants themselves aren’t the problem.
What we talked about in this episode
Preparing for Chicago flooding and why older basements were designed this way
Tim and I started by comparing notes on sewer backups, especially on the South Side. The deep tunnel system has helped, but the key point is the design of older homes. If you have a house built before the 1960s, the basement was designed as part of the city’s overflow relief system. There is usually a sewer access point in the middle of the basement, and the concept was that when the sewer system took in too much water, it would push into basements and then pull back down as the system cleared. The system is better now, but the design reality is still there.
The two best prevention moves: backflow and building up
We talked through the two practical options that actually reduce the risk.
First is installing a backflow system, a one-way valve so sewer water can’t come up through the drain.
Second is building up if you are finishing the basement, meaning don’t build your finished floor directly on the slab. Raise the living area so if water comes in, it hits the lower zone first and you’re not instantly flooding the living space. That can be tough in low ceiling basements, but it is still a real mitigation strategy.
Layout strategy: don’t put the bedroom near the sewer area
We also talked about designing around the sewer location. If the area where the sewer backs up is near utilities, keep the main living space farther away. Some properties have the furnace and utilities closer to the sewer zone and the raised living area farther away, which helps limit how disruptive a backup becomes.
I also mentioned something I’ve seen in some bungalows and single families: a small cement build-up around the drain area that can corral water into one zone if it does back up.
One thing I hate in basements: carpet
I said it directly, carpet in basements makes me cringe. It holds moisture and contamination, and once it gets wet it becomes a much bigger problem.
We compared older basement finishing approaches like tile, which got costly and cracked, to why vinyl plank became a game changer for basements, especially with uneven slabs and water risk. I shared that we tried plank flooring on one of our South Side properties back in 2013, and now you see it everywhere.
We also talked about the maintenance advantage: if one plank gets damaged and you can’t match it perfectly, it’s still easier to blend than a tile floor where one cracked tile turns into a patchwork problem.
Turning maintenance problems into design: tile patterns and accent walls
We got into a practical landlord hack. When you can’t find matching tile, we’ve turned it into a design by creating borders or patterns. In one case, the tile patch ended up looking like a heart shape, and the tenant loved it.
Tim shared a similar idea with paint. If an old paint color won’t match because of fading, turn that wall into an accent wall instead of repainting everything.
We also discussed why spot painting rarely works and why painting the entire wall is the minimum if you want it to look right. We both use standard colors across our portfolios, but even with the same exact paint, age and sun fading means spot painting almost never matches.
Stop storing paint cans and personal property in basements
We talked about how owners keep paint cans in basements like they’re saving money, but it becomes a fire hazard and the paint isn’t good after sitting around. The better move is taking a photo of the paint label and saving it.
We also agreed owners should not leave personal property in rental basements. It’s not worth the risk of damage or loss. If it matters, put it in a storage unit.
ADUs breaking news: the ward map and what it means
We shifted to ADUs and pulled up the new map that shows which wards opted in and which did not. We talked through the categories: fully opted in wards, partially opted in wards, not opted in wards, and areas shown as not eligible.
Even in the wards that opted in, there are still limitations like how many ADUs can be approved per year or per block. So this is going to be a complicated few years as everyone figures out what can realistically get built.
We also said the part that frustrates investors: Chicago is doing a “good thing” but with enough red tape that it may still be too expensive for a lot of owners to convert illegal units into legal units.
Tim also brought up a related point: there are scenarios where adding units can tie into incentives and tax breaks, and in courtyard buildings there may be opportunities to add multiple garden units. But the rules change once you add more than one unit because affordability requirements can kick in.
Taxes, the new assessor, and why small properties feel squeezed
We talked about Cook County’s new assessor and why taxes have felt so random for small landlords and homeowners. The point we discussed is that when major commercial properties get assessed lower, more of the tax burden shifts onto smaller properties.
We also clarified that the assessor is dividing up the tax burden, not setting the total budget, which is why it’s a position where someone will always be upset.
We also talked about vacant commercial space and how broken the incentives can feel in Cook County, where vacancy can become the least bad option for some owners, even though it hurts neighborhoods and small businesses.
CHA issues: the CEO mess and why the program frustrates landlords
We wrapped with CHA because it keeps trending.
Tim summarized the CHA CEO situation and how it’s turned into a political fight. CHA fired the CEO again, the mayor wanted to appoint Alderman Willie Burnett, Burnett stepped down early and his son became alderman without anyone voting, the CHA board hired someone else with experience from Washington DC, and now the mayor is threatening to fire the person the board hired.
Then we talked about the operational problems that make landlords hate the program.
Inspectors quit often.
CHA schedules inspections the night before.
Routes make no sense, bouncing all over the city.
We’ve seen multiple inspections in the same neighborhood handled by different inspectors on the same day.
Both of us said the same thing. The tenants are not automatically the problem. The program is the problem, and the hoops discourage landlords from cooperating because the experience is chaotic and unpredictable.
We also compared it to other housing authorities outside the city where responses and consequences can be faster and more consistent when problems happen.
Questions We Answer in This Episode
Q: Why do older Chicago homes get basement backups during storms?
A: Many pre-1960s basements were designed as relief for sewer overflow, so when the system is overwhelmed, water can push into basements before draining back down.
Q: What is the best fix to stop sewer water from coming up?
A: A backflow system, a one-way valve that prevents sewer water from backing up through the drain.
Q: If I finish a basement, how do I reduce flood damage?
A: Build up the living space off the slab and design around the sewer zone so the main living area is farther away from where backups occur.
Q: What does the new ADU map actually change?
A: It shows which wards opted in, partially opted in, or did not opt in, but even opted-in wards can have limits per year or per block, so approvals will still be constrained.
Q: Why is CHA so difficult even when tenants are fine?
A: The program operations are chaotic. Inspectors quit often, inspections are scheduled with short notice, and routing is inefficient, which creates delays and frustration for landlords.
Show Notes and Timestamps
00:16 Week 12 kickoff and Tim closing on his flip tomorrow
01:47 Deep tunnel discussion and South Side sewer backup reality
02:07 Why basements in older homes were designed for sewer overflow relief
03:10 Backflow systems and why they matter
03:40 Building basement living space up off the floor to reduce damage
05:10 Designing around sewer zones and keeping living space away from backup points
06:06 Why carpet in basements is a bad idea
07:18 Vinyl plank versus tile and why it became the basement standard
09:22 Accent wall trick and why paint fading kills spot paint jobs
11:05 One-wall minimum paint rule and standard portfolio colors
12:28 Stop storing paint cans and personal property in basements
14:24 New Cook County assessor and why taxes shifted onto small properties
20:12 Vacant commercial space and why Cook County incentives feel broken
23:09 ADU map, opt-in wards, and why limitations still matter
32:20 CHA CEO firing, mayor conflict, and why the program stays chaotic
Key Takeaways for Chicago Landlords
If you own an older house, plan for sewer backups because the basement design was built around overflow realities.
Backflow systems and building up a finished basement are the two biggest practical mitigation moves.
Vinyl plank is a better basement flooring strategy than carpet or cheap tile in flood-prone environments.
The ADU map is progress, but real approvals will still be limited by ward rules and red tape.
CHA is still weighed down by leadership chaos and broken operations, which is why landlords struggle with the program more than the tenants.
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
