Remember that old saying that truth is stranger than fiction? Our friend and Straight Up Chicago Investor podcast guest, Joseph Pochinskas, found himself in the landlord twilight zone with his first investment property. 

A Southside Chicago native, Joseph fell in love with the Bridgeport/Canaryville area and decided that’s where he’d try his hand at house hacking. After a lot of research and walking properties, he settled on a four-flat apartment building in Canaryville that was within his price range. 

Joseph bought the property in November 2020 with plans to move into the vacant unit the following January when his own lease ended. 

New Landlord Introductions

After closing, Joseph held a tenant meeting, letting them know he was the new owner and was planning building renovations. Joseph welcomed all the tenants to stay during renovations. (Side note: Avoid planning major renovations in tenant-occupied buildings.)

During the meeting, he outlined his expectations for simple things like not smoking in the building and cleaning up after pets. Naively, Joseph thought this would set up good landlord-tenant relations. What he hadn’t realized was he’d simply advertised he was new and they could easily take advantage of the situation.

Within the first week, he received a call from a neighbor that the police were at his apartment building because two of his tenants were in a brawl. Turns out “not brawling” wasn’t on his list of tenant expectations. Joseph’s mentor advised him not to get involved and just let the police handle it. Ultimately, Joseph never addressed the situation at all. 

Other Issues Emerge

Police visits for brawling tenants were only the beginning of his issues, as Joseph would soon find out.

Missing Rent Records

Joseph’s first mistake happened long before the tenant meeting. Rather than pressing for proof of rent roll, he trusted the previous owner’s claim that every tenant was current on their rent. The previous owner gave him a paper with handwritten ledgers and Joseph took it at face value. Yet, he quickly learned exactly zero tenants were paying rent at all. Naturally this created an instant cash flow situation.

Missing Background Checks

Joseph's next mistake was not asking for any background about the current tenants. In addition to believing the previous owner’s account of the rent payments, he also failed to ask for any background checks on the current tenants. He also failed to conduct any of his own screenings. 

Doing so would have uncovered one tenant with multiple evictions on his record and multiple issues that involved police reports. In fact, during the first few months, before Joseph had even moved into the vacant unit, the police had been called on one problematic tenant no less than a dozen times.  

And Now… A Missing Car

At the beginning of January, Joseph moved into the vacant flat and began renovations on his own unit. Several friends were helping him paint and do minor repairs. One went to retrieve something out of his car only to discover it was missing.

Finding the Culprit

Since someone had stolen the car while parked right outside the building, Joseph spoke to his tenants to see if they’d seen anyone. He even asked one of the tenants with a security camera if he could see the footage. 

Weirdly, the tenant declined, but suggested they consult with a neighbor across the street who had a great video security system. (Hello, red flag!) Upon reviewing the neighbor’s recording, Joseph saw the car thief was the younger brother of the tenant who’d sent him across the street. 

Chicago Blue’s Crime Advice

After a visit to the police station with a copy of the footage, he was faced with two options: try to get the car back himself without involving the police or involve police and face the potential of decades of retaliatory vandalism. 

The police recommended the first option and Joseph agreed. However, he smartly asked for a police escort to have the conversation since he didn’t know what else the tenants may be involved in. Bear in mind these were the same tenants involved in that Week 1 brawl and now were filmed committing a carjacking.

The police informed the tenants that should the car “spontaneously reappear” within 24 hours, there would be no charges. The next morning, they received a call that the car was sitting in the middle of a nearby alleyway. They’d returned the car like a silent apology, “Sorry, man, we didn’t know it was your car.”

Because the car was stolen by a 16-year-old, there wasn’t much he could do apart from telling the tenants to stay away from his stuff. 

You Can’t Make Me Leave

As much fun as that was with a brawling, thieving, non-paying tenant, Joseph didn’t have much recourse. This all happened during the height of the COVID-29 pandemic during the Chicago eviction moratorium that prevented removal of non-paying tenants. Joseph wondered what he’d gotten himself into and how to solve it.

Cash For Keys Snubbed

In an effort to quickly solve the issue, Joseph offered the father a cash for keys exchange. With more than nine family members living in a two-bedroom flat, the tenant knew he had a good thing going. He quickly turned down the offer, stating he had nowhere to take everyone. 

The tenant turned him down, saying he knew he could stay there longer and it would be more valuable than accepting the cash Joseph offered him. Then the tenant dropped the bomb. He told Joseph he’d already been evicted three or four times before and was a professional at this game.

Presenting a Danger to the Building

Joseph contacted the Halsted Law Group for help who advised the only way to evict this amazing bunch was to show they were putting others in danger. 

His lawyer told him to gather evidence, like police reports and videos of tenant misbehavior, so they could begin the eviction process. Joseph learned that between November and March, the tenants received 12 police visits, showing ongoing chaos. 

Water Issues

While this was happening, Joseph received a much higher-than-usual water bill, indicating a leak somewhere. The plumber identified that the source originated from the problem tenant’s unit. 

When Joseph and the plumber knocked on the unit door, the tenants refused to let them in, claiming they had COVID (an excuse used 17+ times previously with Joseph to bar his entry). The tenants then threatened to call the police if they kept knocking. Instead, Joseph called the police since this was a building emergency and the tenants were denying entrance. 

Eventually, the tenants agreed to allow the plumber (and only the plumber) in to do the repair work. The plumbing repair completed, they all went back to their regularly scheduled stand-off. 

Add an Overdose to the List

Several hours later, an ambulance arrived at the building. It turned out the tenant’s mother had overdosed in the apartment. Because of the blue color of her arms, the paramedics determined she’d been that way for hours before they eventually summoned an ambulance. That meant the woman was overdosing and lying unconscious while the plumber was in their unit fixing the leak. 

Eviction Process Activated

Joseph’s attorneys could now move forward with the eviction case, which had nothing to do with the overdose, but rather the building emergency. The tenants had failed to report the leak and then barred landlord and plumber entry to their unit to fix the emergency until police involvement. They were the cause of potential damage to the building and he could evict them.

Of course, these professional evictees played their cards well, extending their court dates. On the day when the judge was set to rule for their eviction, the tenant quickly agreed to be out in two weeks. With this well-calculated move, the tenants moved out at the last possible moment, ensuring another eviction was not added to their public record. 

The Gross Aftermath of Eviction

Ten months into his real estate investing adventure, Joseph finally had the problem tenants out. Now came the fun part of dealing with the mess they left behind. 

Faced with a massive cockroach problem and trash piled a foot deep everywhere, Joseph spent an entire day removing garbage and hired an exterminator to do multiple treatments. Nearly a year after closing and a lifetime’s worth of lessons learned, he finally began all those major renovations. 

Save Your Stuff and Your Sanity

Despite the trouble, there was a silver lining. The situation helped Joseph connect with neighbors, who enthusiastically joined his tenant screening process and shared insights to find better future tenants. Plus, he’s gained confidence in his abilities having survived all the hurdles thrown at him.

Joseph's story shows how dealing with difficult tenants can be a nightmare. 

At GC Realty & Development, we know Chicago property management can be complex and challenging. So we’ve developed a thorough tenant screening process that resulted in zero tenant evictions in 2023, thanks to weeding out applicants with problematic histories. We also outline a proactive maintenance program with an easy maintenance/repair request process. 

By partnering with our experienced Chicago property management company, you can avoid these issues and enjoy a more profitable investment experience. Let us handle the complexities so you can have peace of mind.

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