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Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast
What we talked about in this episode
Chicagoland weather is still creating real landlord problems
We kicked things off talking about the storms that came through the area.
Some places barely got hit. Other areas had heavy rain, funnel cloud warnings, water in basements, and storm-related work orders. At our office, we even had water come into the underground space and had to dry things out in the morning.
We also had commercial tenants dealing with roof damage and entry damage at a shopping center in Woodstock, and they wanted those items addressed before they opened for business.
That is the reality of managing property across the Chicago area. The storm may miss one neighborhood and hammer another. If you own enough property in enough locations, the weather will eventually find you.
The Road to Housing Act could bring some good news
Tim brought up the Road to Housing Act at the federal level, and for once, we had something that was not all bad news for landlords.
There are still political questions around when it gets signed and what version ultimately moves forward, but the bill has a lot of language around cutting red tape, increasing housing supply, improving Section 8 participation, supporting opportunity zones, and helping smaller-dollar mortgages become more available.
My reaction was cautiously optimistic. The ideas sound good. The question is whether the government can actually execute them.
It is easy to say, “Make permitting faster.” It is a lot harder to make a big bureaucracy move faster.
The 350-house cap on large investors
One of the investor pieces Tim explained was the limit on large owners buying more single-family homes.
The way we discussed it, if an investor owns more than 350 houses, they would no longer be able to buy more houses. The important part is that there is no forced sale requirement. They are not being told to sell what they already own. They just cannot keep buying more in that category.
For most people watching Chicago Landlord Secrets, this probably does not apply. We are usually talking to mom-and-pop investors, local landlords, and small to mid-size operators.
If someone owns 500 multifamily units, that is different from owning 350 single-family houses. This is more focused on large single-family rental aggregators than the everyday Chicago investor.
Build-to-rent still appears to stay alive
We also talked about build-to-rent communities.
From what Tim had reviewed, large investors would still be able to build new rental housing. That distinction matters.
Buying existing starter homes is one thing. Creating brand-new rental housing is another. If the real goal is housing supply, then build-to-rent should remain on the table because it adds homes that did not exist before.
We need more housing. More homes, more units, more options. That is what eventually puts pressure on pricing.
Section 8 improvements could be valuable if they work
The Section 8 part of the bill was one of the most important pieces for Chicago landlords.
Tim brought up Section 405, the Choice in Affordable Housing Act. The goal is to expand housing options for voucher holders and make participation easier for landlords.
That matters because landlords usually do not avoid Section 8 because of the tenant. They avoid the process.
The paperwork is slow. The inspections are slow. Items get kicked back. Inspections fail over small things. Vacancy time stretches out. Landlords lose months of rent waiting for the system to move.
One possible improvement Tim discussed was allowing certain federally financed properties to let voucher tenants move in before the inspection is completed, with the inspection still required within a year.
If that works the way it sounds, that could be a major improvement.
Pre-inspections could change the Section 8 conversation
We also talked about pre-inspections.
If a landlord knows they are likely to rent to a voucher tenant, being able to get the inspection done before selecting the tenant could reduce vacancy time. It would make Section 8 easier to work with, especially in areas where voucher tenants are common.
I even said I think housing authorities could charge a reasonable fee for this. If I am a landlord and I know a pre-inspection could help me rent faster, I would gladly pay for that. The value is obvious if it saves weeks or months of vacancy.
This is what we mean by ease of doing business. Landlords will participate if the process makes sense.
The landlord is part of the Section 8 customer base
This is something people miss.
Voucher programs exist to help tenants, but the program needs landlords. Without landlords, voucher holders do not have enough housing options.
That means the landlord experience matters.
If the program is painful, slow, and unpredictable, landlords avoid it. That does not mean they hate voucher tenants. It means the system is hard to do business with.
If housing authorities want more landlords to participate, they need to make participation easier.
A savings path for Section 8 tenants
Tim also mentioned a savings account concept tied to Section 8 tenants.
The idea is that a portion of rent or housing assistance could help create savings for voucher holders, potentially helping them build toward a down payment.
That could matter for landlords too.
If you own a single-family rental and your Section 8 tenant has lived there for years, that tenant might eventually be the buyer. There are programs where housing support can shift from rent support into homeownership support, but many tenants and landlords do not know those programs exist.
If this helps more tenants build toward ownership, that could create a better path for some families and a cleaner exit strategy for some landlords.
Opportunity zones, grants, and zoning reform
The bill also includes more support for opportunity zones, grants, and zoning best practices.
That part reminded us of the Build Act conversation in Illinois. The idea is to push local governments toward better zoning and land-use policies that allow more housing.
In theory, that makes sense. In reality, local rules are often where good housing ideas slow down.
Permits are slow. Codes keep stacking. Villages have their own rules. Approvals take too long. Even when everyone says they want more housing, the process gets in the way.
So yes, cutting red tape is good. But I want to see how it actually works before celebrating too much.
Government regulation is making homes harder to build
Tim brought up a study that said government regulation can add around $132,000 to the cost of a new single-family home.
That number explains a lot.
If regulations, permits, fees, code requirements, and compliance costs add that much to a project, builders are not going to build starter homes. The math does not work. They are going to build higher-end homes because that is where they can absorb the cost.
That is how we end up with the same problem everyone complains about:
Not enough starter homes
Not enough middle-class housing
More renters staying renters longer
More pressure on rent prices
Some safety rules make sense. But at some point, the total cost starts working against the basic need for housing.
Property taxes are one of the biggest rent drivers
We also got into property taxes because this is one of the biggest reasons rent keeps rising.
I had Pat Hines, the incoming Cook County Assessor, on the podcast, and one of the points we discussed is that the assessor’s job is to distribute the tax burden fairly across parcels.
But the bigger question is why the total budget is so high in the first place.
If the county, city, and local governments spend billions, that money has to come from somewhere. It lands in property taxes. Then property taxes land in rent.
People blame landlords for rising rents, but when taxes double or triple, owners cannot absorb that forever.
Dolton mayor eviction story and the lease lesson
Then Tim brought up the Dolton mayor story.
The landlord lesson was simple. Tiffany Henyard was reportedly living in a rental where back rent was owed, but the judge ruled she was not liable because she had not signed the lease. Her boyfriend was liable, but she was not.
That is the takeaway for landlords.
Every adult over 18 needs to apply, be screened, and sign the lease.
If someone is living there and they are not on the lease, you are creating problems for yourself. If the person who signed the lease leaves, you may be stuck with another adult in the property who was never screened and may not be financially responsible under the lease.
How to spot unauthorized occupants
We talked about signs that someone else may be living in the property.
The obvious one is mail. If another name starts showing up on the mailbox or junk mail starts arriving for someone who is not on the lease, that is a red flag.
Other signs include:
A new name on the mailbox
Mail piling up for unknown people
The same person always being present during visits
Extra cars that never leave
Hallways, basements, or storage spaces being used like living space
Tim shared a wild story about someone living in a hallway and claiming residency because mail was being delivered there. They had to go through a legal process to remove her.
That sounds extreme, but if you manage property long enough, you will run into extreme situations.
Unsafe basements create serious liability
We also talked about people using unfinished basements as living space.
This happens more often than it should. Someone turns a basement into a bedroom. A commercial tenant starts sleeping below the restaurant. Someone uses a space that has poor ventilation, low ceilings, or only one way out.
That is a real liability.
I shared a story about a commercial tenant near 65th and Cottage Grove who had basically set up a home in the basement of a restaurant. I respected the hustle, but that did not make it safe. If something happened, it would have become the owner’s liability too.
You cannot ignore unsafe living conditions just because the person has a tough situation or because they are trying to save money.
4th of July prep for residents
We closed with a reminder for landlords heading into the 4th of July.
The funny thing about the 4th is that you may not get a ton of work orders, but the ones you do get can be big.
Fires. Fireworks landing on roofs. Grill issues. Smoke. Noise complaints. Porch problems.
This is the time to remind residents:
No grilling on porches
No open flames where they do not belong
No fireworks on the property
Keep noise under control
Use the yard responsibly if the property has one
If your property has a yard, keep it usable. Residents want to enjoy it, especially around a holiday. But you also need rules before the problem happens, not after.
Questions We Answer in This Episode
Q: What is the Road to Housing Act trying to do?
A: It is aimed at increasing housing supply, cutting red tape, improving voucher participation, supporting small-dollar mortgages, and pushing better zoning and land-use practices.
Q: Does the 350-house cap affect regular Chicago investors?
A: Probably not. It is aimed at very large single-family rental owners, not the typical mom-and-pop landlord.
Q: Why would Section 8 pre-inspections help landlords?
A: Because inspection delays create vacancy loss. If landlords can get units pre-inspected, more may be willing to participate in the voucher program.
Q: Why is new construction so expensive?
A: Regulations, code requirements, permits, fees, and compliance costs keep stacking, which makes it harder to build starter homes.
Q: What is the landlord lesson from the Dolton mayor eviction story?
A: Every adult living in the property needs to apply, be screened, and sign the lease.
Show Notes and Timestamps
00:12 Welcome to Chicago Landlord Secrets and the weekly streak continues
00:34 Heavy rain, funnel clouds, and weather issues across Chicagoland
01:16 Water in the office and storm-related work orders
02:11 Road to Housing Act and why this bill has some good news
04:03 350-house cap for large single-family rental investors
04:52 Build-to-rent carveout and why adding supply matters
07:07 Section 8 improvements and inspection changes
08:39 Pre-inspections and why landlords would pay for speed
09:55 CHA’s customer service problem with landlords
10:37 Why landlords avoid the system, not necessarily the tenant
12:17 Savings accounts and homeownership paths for voucher tenants
13:24 Opportunity zones, grants, zoning, and cutting red tape
15:04 Government regulation cost on new homes
16:38 Why starter homes are no longer economical to build
17:15 Conflicting code requirements and why construction costs keep rising
20:33 Cook County taxes, budgets, and rent pressure
28:45 Tiffany Henyard lease lesson and why every adult must sign
30:15 Screening every adult and watching for unauthorized occupants
31:24 Mailbox names and mail as a red flag
32:03 Hallway occupant story and legal process
34:37 Unsafe basement living situations
36:36 4th of July work orders, fireworks, grills, and porch safety
38:51 Closing thoughts and how to reach Mark and Tim
Key Takeaways for Chicago Landlords
Weather is becoming a bigger operating issue, and landlords need to plan for water, roofs, and emergency response.
The Road to Housing Act has landlord-friendly pieces, especially around supply and voucher participation.
Large single-family rental investors may face limits, but most local landlords are not the target.
Section 8 improvements only matter if the system becomes easier and faster for landlords to use.
Regulation and code costs are a major reason starter homes are not being built.
Property taxes are one of the biggest forces pushing rents higher.
Every adult living in the property needs to apply, be screened, and sign the lease.
Unauthorized occupants can create legal and safety problems fast.
Before the 4th of July, remind residents about grills, fireworks, noise, and safe use of outdoor space.
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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