Vendor Portal
Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast
Winter is almost here, holiday collections get harder every year, and landlords still need clear playbooks when police get involved at a rental.
This week on Chicago Landlord Secrets, Tim and I covered practical snow and salt routines before the first real cold snap, why December rent follow-up matters more than most owners think, and several real examples of how crime-free rules, court process, and documentation can change outcomes when something serious happens at a property.
We also checked in on school board results that matter to property owners, a Springfield rental registry referendum, fee disclosure changes under Illinois' new rental fee rules, and a few lawsuits landlords should keep on their radar.
School Board Results Still Matter To Property Owners
We opened with the school board election because property taxes and school funding stay tightly connected in Chicago.
The big win Tim highlighted was the school board president race. Jessica Biggs won Chicago's first election for Board of Education president, which NBOA viewed as an important outcome for housing providers.
I also admitted I woke up thinking it was the first mayoral race. It is not. That contest is later, so Chicago landlords still have months of campaign noise ahead.
The practical point is simple. Local elections shape taxes, schools, and housing policy. Paying attention is part of owning rental property in this market.
Security Deposits In Chicago Create More Risk Than Reward
Before the news items, we got into one of the most Chicago-specific landlord traps: security deposits.
National advice often treats deposits as non-negotiable. In Chicago, the rules, the claims process, and the courtroom reality are very different.
Tim said his company does not hold security deposits. I shared why we have been unwinding many of ours. Even when you follow the process carefully, defending a deposit lawsuit can cost more than the amount you withheld. A few hundred dollars in deductions can turn into attorney fees in the $1,500 to $2,000 range, plus time, stress, and court appearances.
We also noted that more cases are moving back to in-person court instead of Zoom, which adds parking, travel, and lost work time.
The takeaway is risk management. For many Chicago operators, avoiding the deposit fight altogether is cleaner than winning one after months of distraction.
Springfield's Rental Registry Vote And Why Chicago Landlords Should Watch
PRO and FAIR were quiet again. Tim's read was that City Hall is focused on getting a budget done before the new year, so those competing rental proposals have not moved.
What did move was a Springfield, Illinois advisory referendum. On the November 3 ballot, voters were asked whether the city should adopt a landlord registry, inspection, and licensing program similar to other Illinois cities. Nearly 70% voted yes. The measure is nonbinding, so City Council still has to decide whether to create a program.
Tim was careful to say it does not automatically create a law. It tells local officials that voters want landlords registered and inspected. Our concern is the signal. If a city outside Cook County leans that way, Chicago advocates can point to it when pushing similar registration ideas.
Registration is often the first step. Inspections tend to follow. That is why owners should watch these votes even when they happen outside Chicago.
Police Action, Crime-Free Rules, And Faster Paths When Safety Is At Stake
A big part of this episode was what actually happens when police get involved at a rental.
Tim told a story from a building in Calumet City. There was a shootout involving someone in their building and someone across the street. Police arrested the other party, identified Tim's resident, found guns in the unit, and found what Tim described as a display setup used for selling drugs.
The useful operational point was not the drama. It was the process. Their crime-free team found a filing path that shortened the eviction timeline to about three months instead of the more typical eight-month path, because of the endangerment issues involved. The person who fired was already gone. The remaining work was getting the other occupants out faster than a normal case.
I shared a Glenwood example where police raided a house after unusually high electricity use pointed to a large grow operation. The garage also held a large number of catalytic converters. Even with the residents in jail, possession still had to be recovered through the legal process. Crime-free procedures helped skip some of the early court steps that usually slow these cases down.
We also revisited squatters. Police response is still inconsistent, and owners should not assume a call alone solves the problem. At the court level, though, Tim said Cook County squatter cases can now skip the early mediation-style stretch that often burns the first couple of months. That can save roughly two to three months. DuPage has generally moved even faster.
There is tension in the broader policy debate. State conversations keep coming up about rolling back crime-free ordinances, partly because landlords can be restricted in screening while still being pressured when criminal activity continues. Until the rules are clearer, the practical move is documentation, the right attorney path, and using every lawful process available when safety is at risk.
Lawsuits Landlords Should Keep On The Radar
Tim flagged a Seattle case involving an affordable housing operator, GRE Downtowner LLC, which challenged a package of city rental ordinances as an unlawful taking. A trial court dismissed the case. In late October, the Washington Court of Appeals reversed that dismissal and sent the claims back for further proceedings. Nothing is final on the merits yet, but owners are watching it as a precedent case.
I mentioned an upstate New York source-of-income case where landlords challenged forced Section 8 participation. An appellate court held that compelling landlords into the voucher program in a way that forces property inspections raised constitutional problems. Tim's point was that precedents like these matter when Chicago groups later need case law to point to.
Then came a warning closer to everyday operations: a proposed class action accusing Zillow of junk fees on rent payments made through Zillow Rental Manager. The allegation is that card transaction fees show up late in checkout and were not clearly disclosed as optional, and that the extra charge was not in the lease. Zillow disputes the claims and says bank transfer is a free option with card fees disclosed before payment. The larger lesson matches what NARPM has warned about for screening vendors. Using a third-party platform does not automatically protect the landlord. If residents pay rent through a service that adds fees, those fees need clear disclosure in the lease and payment flow, especially with Illinois' fee-transparency rules now in play.
Illinois Fee Rules: Disclose Early And Update Your Process Now
We spent time on Illinois' rental fee transparency and limitations law.
Under the statute, non-optional fees must appear clearly on the first page of the lease, and they also need clear disclosure in rental listings. Application fees, including background checks, generally cannot exceed $50. A landlord may charge more for a third-party background check only when the actual screening cost is higher, the landlord pays that cost up front, and the applicant is billed within 14 days with the provider's receipts.
I shared a practical idea from Crane: one operator is using a clean fee-disclosure image in listing marketing so the property description is not buried under seven lines of fine print. Tim's wish list was a short industry word for total housing cost, meaning rent plus required fees and related charges on one line.
Both of us are treating this as an operations project, not a last-minute scramble. I am breaking the rules into teaching pieces for our team and process updates. Tim is reviewing leases and recording short explainers, starting with application fees. If you use a board lease, do not assume the updated form arrives on your preferred timeline. Build your own checklist now.
Snow And Salt: Simple Rules Before The First Real Storm
We recorded this on November 5, with first frost expected the next day, so snow planning was timely.
Tim's rule of thumb:
Put salt buckets at buildings so residents can treat walks if snow hits overnight and crews cannot reach every property before morning rush.
Focus on sticking snow. Light flurries that will melt quickly are usually not worth a full deployment.
About 2 inches is the point where they send people out, as long as a quick warm-up is not already on the way.
I added a hard-earned lesson: pick up leftover salt bags when the season ends. Bags break, kids play with them, and you end up with a messy hallway that cleaners have to chase.
On pricing, Tim said owners often choose between per-push and seasonal. For a standard three-flat, he ballparked about $96 per push or around $1,440 for a four-month season. Most of his clients, and his own properties, take the per-push option and effectively bet on a milder winter. Commercial accounts are often per-push anyway. Fuel costs are higher than last winter, so some increase should not surprise anyone.
The goal is not perfection at 3 a.m. The goal is a plan residents can use immediately, plus a clear trigger for when professional service goes out.
Holiday Collections: Stay Early, Stay Consistent
We closed on rent collection because the calendar is about to work against landlords.
Tim described two different collection seasons. Holidays are harder. Once you get past early December, money gets tight fast, even for residents who are usually only a little late. Tax season is the reverse. April is often his strongest catch-up month because tax refunds help residents clear balances.
His advice for right now is direct. Talk to residents early, aim for payment on December 1, and do not wait until mid-month. Consistent follow-up matters more in November and December than in quieter months.
I agreed. I told Tim last month that October would be our best numbers until March. We also build payment plans that can include a tax-refund catch-up for residents who will receive one.
Squeaky wheel gets the grease. In a practical, professional way, that means clear reminders and early conversations before holiday spending crowds out rent.
Questions We Answer in This Episode
Q: When should a landlord send snow crews out? A: Tim focuses on sticking snow and generally uses about 2 inches as the trigger if temperatures are not about to melt it quickly. Salt buckets help residents cover the gap overnight.
Q: Is December really a harder collections month? A: Yes. Tim said holiday season squeezes resident budgets, so early December outreach matters. April, helped by tax refunds, is often a stronger catch-up month.
Q: Can police involvement speed up an eviction? A: In some crime-free situations involving endangerment, Tim said the process can move faster than a standard case. Owners should work with counsel and local procedures rather than assuming every police call creates a shortcut.
Q: Did Cook County change anything for squatter cases? A: Tim said court process can now skip the early mediation-style period in squatter cases, which may save about two to three months. Police response on-site can still be inconsistent.
Q: What fee issue should landlords fix now? A: Disclose required fees clearly in leases and marketing, follow the Illinois application-fee limits, and do not assume a third-party payment platform protects you if add-on fees are not disclosed.
Show Notes and Timestamps
00:26 School board election results and why owners should care
02:43 CIC property management training at GC Realty
04:54 Chicago security deposits and lawsuit risk
09:29 PRO/FAIR quiet while the city works on the budget
09:54 Springfield rental registry and inspection referendum
13:03 Crime-free debate and state-level conversations
14:02 Police action story and faster crime-free eviction path
16:25 Glenwood grow-operation case and possession recovery
17:50 Squatter court timing improvements in Cook County
18:53 Seattle landlord appeal and related precedent cases
20:51 Zillow junk-fee lawsuit warning for landlords
22:43 Fee disclosure ideas and Illinois fee-rule preparation
28:37 Snow, salt buckets, and the 2-inch service trigger
31:28 Per-push versus seasonal snow pricing
34:55 Holiday collections and tax-refund payment plans
Key Takeaways for Chicago Landlords
Local elections and nearby city referendums can shape the next wave of rental rules, even when PRO and FAIR are quiet.
In Chicago, security deposit risk is often about defense cost and stress, not only whether you were right.
When police and crime-free procedures apply, the right filing path and documentation can shorten an otherwise long possession timeline.
Fee transparency is an operations project now. Third-party platforms do not remove the landlord's disclosure duty.
Snow readiness is simple: salt on site, a clear inch trigger, and a service plan before the first sticky storm.
Holiday collections favor early, consistent communication. Build tax-refund catch-up into payment plans where it fits.
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
%20(3)%20(1)_3.png)
_1.png)
