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Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast
This week I hopped on with Tim and we both joked about how we’re evolving. He finally got his camera setup dialed in, we talked about that weird in between weather, and then we got into what’s actually happening on the ground right now for landlords, property managers, and investors heading into spring.
We covered a gas leak situation I’ve never seen before, why chimneys quietly create some of the biggest winter emergencies, what should be on a real spring maintenance list, how squatters are still a mess and what I’m recommending for vacants, why landlord associations matter in Chicago, what this winter did to leasing demand, how we structure leases to avoid the dead months, and a few practical ways to reduce vacancy and reduce scams.
A gas leak problem I’ve never seen before
Tim opened with a situation that surprised me because it’s not a normal “loose fitting” type issue. They had a vacant house in Naperville and during a showing another agent reported a gas leak. They did the right thing immediately, followed protocol, had Nicor come out, and Nicor shut the gas off.
Then they sent a plumber and an HVAC guy, and what they found was wild. The copper gas line coming off the furnace had multiple holes in it. Not one hole. Tim said it looked like eight or nine separate leak points.
He’s still trying to trace the cause, and the only plausible theory so far is that Nicor was doing work in the street recently and something related to pressure being high or low may have contributed. Either way, it’s one of those reminders that even after decades of management you still see brand new problems.
Chimneys can shut your gas off at the worst possible time
I told Tim I’ve never had the “holes in the pipe” thing, but I have seen plenty of situations where Nicor or the fire department comes out because a CO detector goes off, or someone reports a smell, and they discover an issue with the chimney or flue. Sometimes it’s cut off. Sometimes it’s detached. Sometimes it’s the liner. Sometimes wind is pushing air in the wrong way.
And the part that gets people crushed is timing. This never happens when it’s 30 degrees out. It happens when it’s brutally cold. They shut your gas off, and they don’t come back until it’s fixed. Now you’re trying to get a chimney vendor on a Saturday when it’s freezing, and you might not get anyone until Tuesday. In the meantime you still have to keep the unit warm to avoid frozen pipes, so you’re either relocating the tenant or dropping off space heaters and scrambling to stabilize the property.
Tim made a point that I agree with completely. A lot of buyers skim right past chimney items during inspection because it’s not actively failing at that moment. The liner is one of those components people ignore until it becomes an emergency.
Spring prep starts with the boring stuff that prevents expensive calls
Tim brought up spring cleaning and preventative maintenance, and I like that framing because spring is where you can remove a lot of future pain if you do the basics.
Here’s what we talked through.
Furnace and boiler work is mandatory, AC work gets treated like optional even though it should not be
Tim said for them the fall furnace cleanings or boiler fire ups are mandatory, and they’ve got years of data showing that when they got strict about it, maintenance costs dropped. They used to deal with owners pushing back, asking to do it every other year, and they’ve seen firsthand how that decision comes back around.
On the front end, their AC cleaning is optional, but they’re pushing it harder this year because they have data comparing the properties that did it versus the ones that didn’t. He said it’s not a money making play for them, it’s because life is easier for everyone, especially the tenant, if you handle it in May for a small cost instead of losing AC when it’s 95 degrees.
Gutter cleaning is one of the most argued about items, and it’s always the wrong argument
Tim said they get pushback on gutter cleaning, and I agree with his observation that the people who push back tend to be the same people who have bigger problems later.
Spring storms dump debris into gutters, and when gutters overflow, water rolls back onto the roof, fascia, brick, siding, and it accelerates deterioration. Tim explained it well: you don’t need the whole gutter packed. Sometimes a handful of leaves or sticks blocks a section, and now the downspout doesn’t do its job.
That one “small” issue becomes the dumb problem chain where water backs up, freezes and thaws, pushes up shingles, water gets under, and then you find a wet spot above a window. Then a resident sees the wet spot and now you’re talking about mold concerns, health concerns, and a bigger headache than the original gutter cleaning would have ever been.
Caulking is a cheap fix that stops expensive detective work
We talked about caulking around windows, tubs, and general sealing. I said one of my favorite time wasting situations is when a tenant reports a leak, you send a plumber, they can’t reproduce it, nothing shows up, and then the next shower it leaks again.
Half the time it’s not a pipe leak. It’s water getting outside the shower area because the caulk around the tub is shot, or water is hitting the wrong area and escaping. If you have a resident who’s been there three to five years and nobody has checked the tub caulk, that’s a very real risk.
Tim added a line from a property manager friend that I love because it’s true. Windows don’t leak. Glass doesn’t leak. What leaks is what’s around it, above it, below it, the ledges pitched wrong, and the spots where water collects.
Chimney caps are cheap compared to what happens without them
We also talked about chimney caps. Tim called it an inexpensive fix and noted it’s code in Chicago to have a cap. He said it’s typically a few hundred bucks depending on height and access.
Then he told a story that made the point perfectly. When he bought his personal house in Tinley, the sellers were literally chasing birds out during the inspection because birds got in through the chimney since there was no cap. The first thing he did was install the cap because that whole situation is ridiculous, and completely avoidable.
We also talked about wind. Tim explained that certain wind patterns can blow down the chimney and mess with pilot lights or burners, and the cap helps prevent that at least some of the time.
The shower curtain problem is more real than people want to admit
We went into something that sounds silly until you’ve lived it.
Tim said on the South Side they ran into issues where people simply didn’t use shower curtains. I said I’ve seen a different version where the tenant has a curtain but doesn’t understand that the liner goes inside the tub, not outside. If the curtain stays outside, water hits it, bounces, and ends up on the floor.
I joked that we added a shower curtain to the Straight Up Chicago Investor merch store and we’ve literally sent it to tenants before as a preventative measure. It’s funny, but it’s also real. Water damage into the unit below is not funny when you’re the one paying for it.
Squatters are still a problem, so I’m focused on proof and process for vacant units
Tim asked about squatter updates, and I told him I don’t need everyone thrown in jail. I want them out of the house. Enforcement is inconsistent, and Illinois is not a place where you should expect someone to sit in jail for long anyway.
What I said matters is what the law seems to require right now. There needs to be some kind of forced entry element for police to be more willing to act. So my recommendations for clients with vacants have been focused on creating proof that supports forced entry and supports removal.
- Put alarms on vacant properties.
- If the alarm company calls the police about a break in, it’s easier to get action than if you just call and say someone is squatting.
- If there is a break in, make a police report immediately, even if the person ran before police arrived.
- If the property gets breached, secure it fast, board it up if needed, and document everything.
Tim told a story that was crazy and honestly kind of impressive in a bad way. Someone broke into a building that had an alarm, took the alarm, and put it in the freezer. He said his Simply Safe rep told him that apparently it’s common, which is insane, but the point stands. People are trying to defeat the systems.
Tim also mentioned he’s heard of people registering vacant units with police departments in certain villages, but he doesn’t know how widespread or effective that is. We also talked about how in Chicago, if the whole building is vacant for a certain time, you’re supposed to register it. It’s less common with two flats and four flats since the whole building is rarely vacant, but it matters if it is.
Why landlord associations matter in Chicago
We shifted into the bigger picture. I brought up the NBOA Neighborhood Building Owners Alliance, also called NBOA, and how they support small investors and small housing providers across Chicago.
I explained it simply. If you like what Tim and I do here, talking real estate and management and trying to make landlords stronger, NBOA does that at a city level. They’re connected with other industry groups and they’re active in advocacy. They also have neighborhood groups, and I listed examples like South Side, Edgewater, Rogers Park, Lincoln Park, and Northwest groups. The point is there are local networking options depending on where you invest.
Tim said something that I think every landlord needs to understand. Tenants have many tenant rights groups with funding and representation, and those groups are in the ears of lawmakers constantly. When lawmakers only hear one side, they assume the majority wants that outcome. That’s why groups like NBOA and others matter, because they bring the other voice, and they point out the unintended consequences.
I agreed and gave an example of how the Cook County tenant rules that came out in 2021 could have been far worse without landlord groups at the table helping shape it.
We also talked about evictions because it ties directly to why the rules matter.
Eviction timelines are not an Illinois problem, they’re a Cook County problem
Tim asked about the eviction timeline outside of Cook County. The number that came up was that in DuPage and Kane, you should be able to go from filing to having them out in about 90 days.
And then I said what matters for investors. That means the slow eviction timeline is not an Illinois problem, it’s a Cook County problem. That delay changes everything. It increases risk, which pushes rents higher, and it forces more strict screening. I said it directly. If I could get someone out in 60 days, I’d probably give more people chances. But if the risk is ten months of lost income, I can’t take that chance for a client.
That’s why I keep circling back to involvement. Giving time and money to groups that advocate for housing providers matters because these laws change your underwriting.
Leasing finally bounced back, and the weather was a big driver
We talked about how rough this leasing winter was. Tim said it was one of the roughest leasing winters they’ve had, driven by cold, ice, and showing volume being way down in November, December, and parts of January. Then they started seeing a big uptick, even on listings that had been sitting longer.
I shared the same pattern on our side. We came out of Christmas gung ho like we usually do, then showings hit a halt for about three weeks and it didn’t matter what you did. Dropping price wasn’t going to create demand if nobody is going outside.
Then it springboarded forward. We leased more in the last couple weeks than we did in the previous couple months. That slowdown created pent up demand, and it also created moments where multiple quality applications came in at once, which helped with negotiating move in dates and avoiding unnecessary price drops.
We tied it to weather reality. When it’s negative thirty with wind chill, nobody is touring if they don’t have to. When it’s suddenly 65 and sunny, people stop doing work and go enjoy the day. The leasing market rides those swings hard in Chicago.
We also talked about seasonality shifting over the years from the Great Recession to COVID and how the same work still gets done, but it gets compressed into a smaller window, which can make teams panic if they don’t keep perspective.
How I avoid the dead months, and how I think about lease timing
Tim asked a very practical question. If you get a December vacancy, are you doing anything with lease structure to get out of that season?
He explained their policy clearly. They don’t allow leases to end in October, November, or December. They’ll do 15 or 16 month leases and push the next end date to no sooner than March 31. He said March 31 is perfect, and even end of February for a March move in is solid because you can be early in the season and potentially bump price a bit.
I told him we do something similar. If leasing is slow we sometimes take what we can, then use renewals strategically with 10 month or 14 month renewals to pull lease ends out of the dead period.
The quiet vacancy killer is the gap between lease signed and rent starting
This is one of my favorite points from the conversation because landlords miss it constantly.
I said you can lease something in four days, but if the tenant doesn’t move in for another 30 days, those four days don’t matter. I don’t care how fast you got a lease signed. I care when money starts coming in.
I also said the gap is negotiable. If someone wants April 1, try to negotiate March 1, or at least March 15. On a $3,000 rental, even two weeks matters. And sometimes the tenant likes it because they can move slowly.
Tim agreed and we talked about another city versus suburb difference.
City renters plan ahead, suburban renters move fast
I said we’ve tracked a big difference in move in timing between city and suburbs.
In the city, especially West Side, Northwest Side, downtown, renters are planning 60 to 90 days out. In places like Schaumburg, people will move next week.
That difference changed how we approach pre marketing and timing, because a lot of landlords wait until a unit is vacant, clean it, and think it will rent in two weeks, but the person wants to move in 40 days later. That gap is where your vacancy leaks out quietly.
Fraud is climbing, and listing theft is part of the new normal
Toward the end I said leasing is fun because you can do deals fast, but scams are getting worse, and the ability to spot BS matters more than ever.
Tim said they’ve already caught multiple fraudulent applications recently, and having software to catch it helps. But the other side is listing theft. Scammers copy your ads, copy your photos, and repost them on places like Craigslist, Zillow, or anywhere else. Then a real person calls and says they already paid first month and a move in fee and want to see the place, and you’re stuck explaining they were scammed.
Tim recommended watermarking photos with your phone number or something similar so it’s harder to spoof. He also said you can set up Google alerts for your name or addresses to help catch copies early.
Then Tim mentioned he has a meeting with a company that does 24/7 scanning for duplicate listings, because even watermarks can be removed now. He said he’ll keep everyone updated on whether that service is worth it.
Leasing is a great entry point for real estate careers, and we’re hiring
We closed with a practical career and hiring segment.
Tim said if you’re a realtor, especially a new one, leasing is a great way to make commissions quickly in spring and summer. A sale might take months, but a lease closes fast. If you can do volume, the math can beat waiting on a single sale.
He also said they’re often looking for leasing agents, and they can train and license people, especially if they’re willing to work the South Side.
On my side, I said we have 1099 showing agents, people who show units around their normal job or on weekends. I also shared that we’re looking for gig style help with move out and move in inspections. You go to the unit, use our inspection app, complete the inspection for a set fee, then return about 10 days later for quality control. We specifically need help on the southwest, south, and southeast sides.
And I said something I believe. If you’ve been “learning real estate” for two years and still haven’t done anything, these kinds of roles are one of the best ways to stop being scared. You learn the real problems you’ll face as an investor, agent, or property manager, while still keeping your normal job.
Questions I answer in this episode
Q: What’s the most important spring maintenance work to prioritize?
A: I’m focused on chimney and liner awareness, gutter cleaning, optional but smart AC cleaning, and basic caulking and sealing around tubs, windows, and doors before small water issues turn into bigger complaints.
Q: Why do chimney issues become emergencies so fast?
A: Because CO detectors, gas leaks, and backdraft issues can trigger Nicor or the fire department, and if they shut off gas, they won’t restore service until the issue is fixed, which can leave tenants without heat in the coldest weather.
Q: What are you recommending to protect vacant properties from squatters?
A: I’m recommending alarms, immediate police reports for any break in, fast securing of the property, and documentation that shows forced entry so police action is more likely.
Q: Why should landlords care about advocacy groups like NBOA?
A: Because tenant groups show up and influence legislation constantly. If housing providers aren’t represented at the table, laws get written without understanding the landlord side, and the unintended consequences often hurt tenants and raise housing costs.
Q: What is the biggest vacancy mistake landlords make during leasing season?
A: Letting too much time pass between the lease being signed and the move in date. The lease signing speed doesn’t matter if rent doesn’t start for another month.
- 00:35 Camera upgrades, Instagram jokes, and that in between weather feeling
- 01:12 Getting ready for spring and building a real spring cleaning list
- 01:43 Vacant Naperville showing, gas leak protocol, and Nicor shutting off gas
- 02:03 Multiple holes in the copper gas line and trying to trace the cause
- 03:29 Chimney and flue issues that shut gas off during brutal cold
- 04:35 Why chimney liners get ignored and why that’s a mistake
- 05:26 Dryer vent cleaning, preventing fires, and avoiding backdrafting issues
- 06:01 Why chimney inspections and repairs are rarely cheap
- 07:34 Chimney caps, Chicago code, and the bird in the house story
- 09:16 Spring maintenance priorities and what’s mandatory versus optional
- 10:04 Furnace cleanings reduce maintenance costs, AC cleaning data, and why it matters
- 10:46 Gutter cleaning pushback and how it leads to roof and masonry issues
- 12:34 Water damage chains, wet spots, and why complaints escalate fast
- 13:24 Caulking tubs, windows, and preventing mystery leaks
- 14:36 Shower curtain issues and why water damage below keeps happening
- 16:44 Squatter enforcement realities and what makes police action more likely
- 18:27 Alarm in the freezer story and documenting break ins with reports
- 20:59 NBOA, landlord representation, and why it matters in Chicago politics
- 23:54 Eviction timelines in DuPage and Kane versus Cook County risk
- 27:10 Leasing winter slowdown, spring uptick, and showings coming back
- 31:47 Lease structuring to avoid October through December ends
- 33:02 City renters plan 60 to 90 days out, suburban renters move next week
- 33:38 The gap between lease signed and move in date as a vacancy killer
- 35:03 Fraud, stolen listings, watermarking photos, and setting up alerts
- 37:22 Leasing as a fast income path for realtors and seasonal hiring needs
- 38:31 1099 showing agents, gig inspection roles, and learning real estate faster
- 40:05 Wrap up and spring weather reminder
Takeaways for Chicago landlords and property managers
- Chimney liners and flue issues can shut off gas at the worst time, so chimney awareness is not optional.
- Chimney caps are a relatively low cost upgrade that can prevent birds, wind issues, and headaches.
- Spring maintenance should include gutter cleaning, caulking, sealing, and smart AC prep before heat hits.
- A lot of “leaks” aren’t pipe leaks, they’re water escaping tubs, windows, or gutters due to failed sealing.
- Vacant property protection is about proof and documentation, alarms and fast police reports matter.
- Cook County eviction delays increase risk, which increases rent pressure and forces stricter screening.
- Leasing demand rebounds hard in spring, so don’t panic price drop during short weather driven slowdowns.
- Avoid October through December lease endings when you can by using longer lease terms and strategic renewals.
- Vacancy is often driven by the move in date gap, negotiate earlier rent start when possible.
- Listing scams are rising, watermarking and alerts can help catch stolen ads before victims send money.
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
