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Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast
Tim and I moved this live from Thursday to Friday, and it ended up being the right call because the Chicago area got hit with heavy storms, power outages, trees down, and power lines involved. That turned into a bigger conversation about what landlords should do when weather damages a property, where renters insurance comes in, how tenant-caused maintenance should be handled, and why Mayor Johnson’s “just cause eviction” proposal is something every Chicago landlord needs to be watching closely.
What we talked about in this episode
Dangerous weather creates landlord problems fast
The storm damage started the conversation. Tim had power outages, a tree hit a power line, and one car in an uncovered parking area in Pilsen had the front bumper torn off by flying debris.
The first rule is simple: if a tree hits a power line, do not try to be a hero. Wait for ComEd to clear it. Until the utility company says it is safe, nobody should be touching anything.
Then you have to figure out where the tree came from. If it is on the parkway, it is usually city property. If it is in the yard behind the sidewalk, it is usually your tree. If it is the neighbor’s tree, you start by trying to work through the neighbor and their insurance.
We also talked about how insurance can get messy depending on the policy. A normal landlord policy, a flip policy, and a construction policy may not treat the same event the same way.
Renters insurance is not optional in real life
A tree through a roof is the dramatic example, but the lesson applies to smaller issues too.
If a storm makes the unit temporarily uninhabitable, the landlord needs to fix the property. But the tenant’s hotel stay, food loss, and personal property loss should usually run through renters insurance.
Same thing with the fridge conversation every landlord has heard before. The fridge breaks, and somehow the tenant went grocery shopping that same morning and bought $400 worth of food. The landlord’s responsibility is to fix or replace the fridge. The spoiled groceries are a renters insurance issue.
That is why renters insurance matters. Not because it solves every problem, but because it gives the resident somewhere to go when personal property or temporary lodging becomes the issue.
Some “maintenance issues” are really tenant education issues
We got into appliances because a lot of calls are not true mechanical failures.
Sometimes a freezer is jammed so full that airflow is blocked. Then the tenant thinks the fridge is broken. Sometimes the dishwasher is not cleaning because they are not using rinse aid. Sometimes they use the wrong soap and create a bigger mess. Sometimes they put plates in with food still sitting on them and expect the dishwasher to perform a miracle.
Garbage disposals are the same. I do not love them in rentals, but if they are there, residents need to know how to reset them and what not to put down them. A lot of disposal issues are either the unit is burned out or the tenant jammed it with something they should not have put in there.
That is where the chargeback conversation starts.
Chargebacks need to happen in real time
Tim asked how we handle chargebacks, and I think this is where a lot of landlords get soft or sloppy.
At move-out, chargebacks are cleaner because you are comparing move-in condition to move-out condition. During the lease, it can be harder because you have to decide if something was normal wear and tear, poor installation, or tenant-caused damage.
But if it is clearly tenant-caused, do not just hold it until the end. Charge it back in real time.
That matters even more in Chicago where most landlords are not holding security deposits. If a vendor goes out because the tenant confirmed access and then nobody is there, that trip fee should be charged back. If the dog was supposed to be caged and the vendor cannot enter, that should be charged back. If there is a lockout or missed appointment charge, that needs to be clear.
And with the new Illinois law starting January 1, those charges need to be disclosed on the first page of the lease. Not just monthly fees. Lockouts, missed appointments, trip fees, and similar charges need to be upfront.
Maintenance access depends on urgency
We talked about residents who want to be home for every maintenance visit.
If it is an emergency or something actively damaging the property, like water leaking into the unit below, we are going in. The resident can be there if they want, but the property has to be protected.
If it is something minor, like a loose doorknob, we can work around the resident’s schedule within reason. But if the delay is because the tenant only wants one specific time, we document that. If the repair takes longer, the record should show why.
Bathroom discoloration is usually a moisture problem
We also talked about “mold” complaints, or what we call discoloration until it is tested.
Older Chicago buildings often do not have proper exhaust fans in bathrooms. That means the tenant has to open a window, wipe down surfaces, and manage moisture. That is not always realistic, and it creates a recurring complaint.
In a perfect world, you install an exhaust fan. But retrofitting fans into older buildings can get expensive if you have to vent them correctly.
The best setup is tying the exhaust fan to the bathroom light. If the light goes on, the fan goes on. That is the only way to make sure it actually gets used.
Move-in condition sets the tone for the entire lease
This was one of the best maintenance points in the episode.
If a tenant moves in and the unit is clean, ready, and everything obvious works, they usually feel good about the home. But if they move in and the first thing they see is a missing light bulb, a dirty corner, or something broken, their brain starts hunting for more issues.
That is why turnover matters.
Do the work before move-in. Clean the unit. Replace the bulbs. Make sure the obvious stuff works. Do not tell the tenant, “We’ll fix that after you move in.” That is how you start the relationship with distrust.
Cheap repairs can cost more long term
Tim brought up a good example with shower cartridges. You might have a cheap part and a better part. The cheap one saves money today, but if it fails in two years and you have to open the wall again, you did not save anything.
Landlords do this all the time. They compare the cheap option today instead of the cheaper option over the next ten years.
We also talked about access panels. They can be great when you need future access to plumbing or electrical behind a wall. But you still need standards, because I once walked into a kitchen where the ceiling looked like it had access panel polka dots everywhere. Good idea, bad execution.
CHA news keeps reminding landlords why the program feels broken
Tim brought up the news about a former CHA head being indicted over alleged contractor kickbacks close to $500,000.
That kind of story makes landlords even more frustrated because participating in CHA is already hard. The paperwork, inspections, packet delays, and lack of consistency create enough friction without the leadership headlines.
Tim said they are currently seeing about 60 days from packet submission to getting a CHA tenant moved in. That creates a real decision for landlords: wait for CHA, or take a market tenant who can move in much faster.
And that is the point we keep making. The issue is not always the tenant. A lot of the time, the program itself is the problem.
Just cause evictions could be a major problem for Chicago landlords
The biggest topic of the episode was Mayor Johnson’s just cause eviction proposal.
The simple version: if a landlord wants a tenant to leave at the end of the lease, but the tenant has not stopped paying rent or clearly broken the lease, the landlord may have to pay relocation fees.
Based on what Tim heard at the MBOA meeting, the numbers being discussed are serious:
If you are owner-occupied and want the tenant above you to leave, it could be 3 months of rent.
If you are not living in the building and want to move back in or have a relative move in, it could be 5 months of rent.
Condo conversion, government order to vacate, significant repairs, or demolition could also fall into the 5-month category.
If the tenant rejects a rent increase or any other reason applies, it could be 10 months of rent.
That last one is the problem. If a tenant rejects a rent increase and the landlord owes 10 months of rent to get possession, that starts looking like rent control without calling it rent control.
Why just cause changes the game
Just cause limits flexibility.
If the tenant is not paying, that is one thing. If there is a clear lease violation, that is another. But a lot of real landlord decisions are not that clean.
What happens if:
You need to do major repairs.
You want to move back into your property.
A family member needs the unit.
You want to reposition the property.
You want to sell.
The tenant refuses a reasonable rent increase.
Those situations become expensive fast.
And lease violations are not always simple either. If the tenant is smoking and you issue a notice, they may say they stopped. If they have an unauthorized dog, they may say they removed it. A lot of violations can be “cured,” which means landlords may still be stuck.
Where this proposal stands
Tim said this could move faster than people think because it may be pushed through the housing committee instead of the normal route.
That is why landlords need to pay attention now. Meeting dates can move. Hearings can shift. If you are waiting until everything is final, you are already late.
MBOA, CAR, Illinois Realtors, and other landlord and real estate groups are pushing back. If you own rental property in Chicago, this is one to track closely.
Questions We Answer in This Episode
Q: What should landlords do when a tree hits a power line?
A: Wait for ComEd. Do not touch anything or send anyone near it until the utility confirms it is safe.
Q: Who pays for a hotel if storm damage makes a unit temporarily uninhabitable?
A: The landlord fixes the property. The tenant’s hotel stay and personal property loss should usually go through renters insurance.
Q: Should landlords charge back tenants during the lease or wait until move-out?
A: If the chargeback is legitimate and clearly tenant-caused, charge it in real time. Waiting until move-out weakens your position.
Q: Why does move-in condition matter so much?
A: Because if a tenant sees problems on day one, they start looking for more. A clean, ready unit reduces complaints and sets the tone for the relationship.
Q: Why is just cause eviction such a big deal?
A: Because it can force landlords to pay large relocation fees even when they simply want possession back for reasons outside nonpayment or clear lease violations.
Show Notes and Timestamps
00:24 Week 20, episode 21, and moving the live to Friday
00:47 Chicago-area storms and power outage issues
01:24 Trees down, power lines, and storm damage reports
02:31 What landlords should do when a tree hits a power line
03:02 City tree vs owner tree responsibility
03:34 Neighbor’s tree falling into your yard and insurance questions
05:16 Tree falling into a house and making a unit temporarily uninhabitable
05:49 Renters insurance and hotel coverage after storm damage
06:17 Fridge failures and spoiled food claims
07:34 Overloaded fridge and freezer airflow issues
08:18 Dishwasher misuse, rinse aid, and wrong soap problems
10:14 Garbage disposals, reset tools, and tenant misuse
11:03 Tenant chargebacks and wear and tear conversations
12:14 Why chargebacks should happen in real time
12:50 New Illinois lease first-page disclosure requirements
13:29 Maintenance access and tenant scheduling conflicts
15:01 Bathroom discoloration and exhaust fan issues
17:35 Wiring bathroom fans to lights
19:18 Move-in condition and how it affects future work orders
21:23 Cheap repairs vs long-term repairs
22:31 Access panels and future maintenance access
25:05 CHA contractor kickback indictment discussion
29:17 CHA delays and why the program is frustrating for landlords
34:36 Just cause eviction proposal
37:24 Relocation fee categories and owner move-in scenarios
38:26 10 months of rent if a tenant rejects a rent increase
39:06 Where the proposal is in the process
41:03 How landlords can track and respond through MBOA and CAR
Key Takeaways for Chicago Landlords
Storm damage starts with safety. If power lines are involved, wait for ComEd.
Renters insurance matters because hotel stays, food loss, and personal property losses are usually not the landlord’s responsibility.
A lot of appliance work orders are really tenant education issues.
Chargebacks should be documented and collected in real time when tenant responsibility is clear.
Move-in condition affects tenant behavior for the entire lease.
CHA delays and leadership issues continue to make program participation harder than it should be.
Just cause eviction could function like rent control if landlords owe massive relocation fees after rejected rent increases.
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
Free Rent analysis: https://www.gcrealtyinc.com/free-rental-analysis
Schedule a call: https://calendly.com/mark-449/looking-for-prop-mgmt
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