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Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast
Chicago winters don’t just bring snow and sub-zero wind chills. They bring the problems landlords and property managers wish they never had to deal with: frozen pipes, no-heat emergencies, vacant-unit risks, and the reality that squatters don’t care what your plans were for that building.
In this Chicago Landlord Secrets livestream, Mark Ainley (GC Realty & Development) and Tim Harstead (Chicago Style Management) get real about what they’re seeing in the field during extreme cold events, and how those same cold snaps amplify one of the most frustrating issues in the Chicagoland market: unauthorized occupants (squatters) and what the law is supposed to do versus what’s happening in practice.
This isn’t theory. It’s two working property managers sharing what they’re doing today to prevent disasters, and what to do when prevention fails.
Why This Conversation Matters for Chicago Landlords
Here’s the honest truth: if you own rentals long enough in Chicago, you’re going to deal with at least one of these situations:
- A no-heat call at night when parts aren’t available
- A frozen pipe that turns into a burst pipe when temps rise
- A vacant unit that becomes a magnet for unauthorized entry
- A police interaction where you hear “civil matter” (again)
Mark and Tim walk through practical “do this now” steps, especially useful for landlords who self-manage and don’t have a system for winter readiness or emergency response.
Cold Weather Prep: The Checklist That Prevents the Worst Calls
Mark and Tim emphasize a simple philosophy: don’t trust that everything is fine just because nobody called yet.
Before the deep freeze hits, their teams are:
- Sweeping buildings (especially basements)
- Confirming heat is working and set properly
- Checking for signs of break-ins in vacant or vulnerable areas
- Winterizing long-term vacants (draining lines, shutting off water, etc.)
- Using portable heaters strategically for cold basement pipe areas
The big takeaway: winter problems don’t always start with a tenant complaint. Sometimes they start with a vacant unit, a locked room, or a basement area nobody’s looked at in weeks.
Space Heaters: A “Buy Time” Tool That Saves Deals and Resident Relationships
When heat goes out at 8 PM, you can often get an HVAC tech there, but you can’t always get parts until morning. That gap creates risk.
They talk about keeping space heaters stocked and using them as a temporary bridge:
- Keeps residents safe and reduces escalation
- Helps protect plumbing from freezing
- Shows “good-faith response” when things are outside your control
Mark also shares a tactical tip that most landlords never consider: using a messenger service to deliver space heaters quickly (instead of driving across town). He mentions using a service like Roadie to move equipment and even keys efficiently, saving hours of time and getting residents what they need faster.
Preventative Maintenance: The Cheapest Way to Avoid the Most Expensive Repairs
Mark shares a classic lesson: landlords will spend thousands in January after skipping a basic furnace check in September.
- Furnace clean/check in late summer or early fall
- Catching small issues before they become emergency failures
- Reducing after-hours calls and “no parts available” situations
They also mention internal data patterns: properties that skip the cleanings tend to rack up dramatically higher spend than those that stay on a preventative schedule.
Frozen Pipes: What Tenants Should Watch For (And What You Should Teach Them)
They outline resident education points that actually prevent burst pipes:
- Dripping water (a true drip, not a running faucet)
- Keeping sink cabinets open on exterior walls to allow warm airflow
- Keeping interior doors open for airflow, especially basements and bathrooms
- Maintaining heat even when traveling (don’t shut it off because you’re in Florida)
- Watching for low water pressure as an early warning sign of freezing
They also flag a big one many owners forget: hoses left on exterior spigots can lead to frozen/ruptured pipes just inside the wall.
The Squatter Transition: Winter Makes Vacancy a Target
Midway through the livestream, Mark transitions into a live issue their team found that day: a leak in a building where they also discovered squatters.
- A maintenance emergency
- A property access problem
- Unauthorized occupancy
- And the clock ticking while damage worsens
In the moment, they got access because the squatters wanted water restored, but they emphasize how quickly this can go sideways when access is denied.
The “New” Law and Why Landlords Aren’t Seeing Real Change Yet
They discuss the Illinois law change that was expected to help remove squatters by strengthening trespassing enforcement.
The problem they’re seeing on the ground:
- Police still hesitate and often default to “civil matter”
- Confusion and risk of being wrong drives inaction
- Even the law’s author has publicly suggested enforcement isn’t matching intent
- Landlords are still getting stuck in the slow lane
Their practical stance: until enforcement becomes consistent, landlords must assume squatters can still become a long, expensive process.
What To Do If You Show Up and Someone Is Living in Your Vacants
They list real-world “show up prepared” items that can help when police meet you on-site:
- Deed / proof of ownership
- A copy of the lease you use (to compare against fake paperwork)
- Utility bill showing you’ve been paying services recently
- Keys (if you can prove access/possession)
- Any camera evidence showing forced entry or unauthorized activity
They also mention a preventative play: for long-term vacants, contact utilities and lock down service activation so nobody can turn on gas/electric without owner authorization.
Q&A
Q: What’s the fastest way to prevent frozen pipe disasters during extreme cold?
A: Combine prevention + resident education. Winterize long-term vacants, keep heat consistent, encourage cabinet doors open on exterior wall plumbing, and teach residents to report low water pressure immediately.
Q: Is dripping water actually necessary, or is that just old landlord advice?
A: It’s still useful, but it needs to be a true drip, not a running faucet. A small drip keeps water moving without spiking bills.
Q: What’s a sign a pipe is freezing before it bursts?
A: Low water pressure. If residents report pressure dropping, you have a window to intervene before it becomes a basement flood.
Q: Why do pipes often burst when it gets warmer, not when it’s coldest?
A: As temps rise, ice expands and shifts as it melts. That transition is when hidden damage reveals itself and water starts flowing where it shouldn’t.
Q: Do space heaters actually help, or are they just a band-aid?
A: They’re a “buy time” tool. When parts or vendors aren’t available immediately, they keep residents safe and reduce risk while you coordinate the fix.
Q: What’s the biggest winter mistake landlords make with vacant units?
A: Leaving utilities active and not checking the property frequently. Vacancies become targets, especially when the weather turns brutal.
Q: If a squatter is inside my unit, can I just change the locks?
A: No. They’re clear that self-help creates legal risk. The situation can escalate quickly, the best move is to document, involve police (even if inconsistent), and take the next legal steps correctly.
Q: What should I bring if I meet police at a squatter-occupied property?
A: Proof of ownership (deed), proof you’ve been operating the property (utilities), your lease template, and anything that supports possession and vacancy status.
Q: Why are police still calling this a “civil matter” even after the law changed?
A: Because the risk of removing the wrong person is high, and enforcement is inconsistent. Officers tend to default to avoiding liability.
Q: How do you reduce squatter risk for a property that will sit vacant for months?
A: Winterize it, shut off utilities where possible, restrict utility activation, add cameras, and increase frequency of property checks.
Q: What’s the long-term fix for the squatter problem?
A: They suggest the pressure needs to stay public. The louder and more documented the problem becomes, the more likely enforcement or legislation evolves.
Show Notes & Timestamps (15 total)
00:33 Chicago deep freeze setup and why this week is different
01:12 Storm cancellations and why property managers plan for “no travel” days
01:50 Chicago Landlord Secrets livestream intro and weekly cadence
03:18 Pre-freeze building sweeps: basements, break-ins, and heat confirmation
04:41 Winterizing vacants and why it’s worth the hour of work
05:10 The “winterized toilet” story and why showing protocols exist
06:01 Stocking space heaters and using them during heat outages
07:12 Messenger services (Roadie) to deliver heaters/keys and save time
08:38 Furnace cleanings: the $85–$100 spend that prevents $3,000 emergencies
10:54 Winter resident tips: dripping faucets, cabinets open, airflow in rooms
13:05 Travel reminder: heat protects the house, not just the people
14:41 Outdoor hose/spigot freeze risk and interior shut-off strategy
16:53 Early warning signs: low water pressure and when to call immediately
21:03 Transition to squatters: active leak + unauthorized occupants in a building
30:00 Best practices when confronting squatters: deed, lease, utilities, cameras
Key Takeaways for Chicago Landlords and Property Managers
- Winter emergencies aren’t rare, they’re seasonal and predictable
- Preventative maintenance saves more than it costs
- Space heaters can protect residents and reduce escalation during outages
- Vacant units need a winter strategy (inspection + winterization + utilities control)
- Squatter enforcement remains inconsistent, documentation and preparation matter
Guest Information
Host: Mark Ainley, GC Realty & Development
Guest: Tim Harstead, Chicago Style Management
Final Thought
Chicago winters are a stress test, not just for buildings, but for landlord systems.
If your winter plan is “react when someone calls,” you’re already behind. The landlords who win this season are the ones who build process into the predictable: furnace checks, vacant inspections, winterization, resident education, and a real response plan for emergencies and unauthorized occupancy.
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
