In early 2021, I received a call from an out-of-state owner looking for property management services. He had a multifamily building in Chicago that was in terrible shape—both physically and operationally.
The situation was dire: the property was falling apart, tenants had been grandfathered in from the previous owner without leases, and in some cases, the owner didn't even have their names or contact information. To make matters worse, all tenants were behind on rent, and many had stopped paying months ago. The previous property management company—a well-known firm in the Chicago —had done nothing but kick the can down the road, leaving the owner feeling hopeless.
I knew this would be a tough one, but I took it on.
I started with a free evaluation to understand the scope of the problem. Once I had a clear vision, I spoke with the owner to determine his long-term plans—whether he wanted to sell or hold the property. His decision would dictate the management strategy. We then developed a 12-month turnaround plan.
Over the next year, I worked through each unit one by one:
I established direct communication with tenants, explaining that improvements were necessary.
We properly removed the non paying tenants in compliance with legal requirements.
I helped the owner secure financing that fit his financial situation.
We executed a cost-effective but comprehensive rehab that could bring premium rent.
We raised rents to market levels and secured high-quality tenants with proper leases.
We implemented an online portal for seamless tenant communication and maintenance tracking.
By the end, the transformation was remarkable. What was once one of the worst-performing buildings—riddled with violations—became a top-performing asset in the neighborhood. The owner no longer had to stress about day-to-day issues; he simply received monthly performance reports while the property ran efficiently.
Key takeaways from this experience:
There’s no magic pill for distressed properties—turnarounds take time and effort.
Set clear expectations with owners so they understand the process.
Focus on the fundamentals: habitability and tenant management and effective operations.
Communicate honestly and respectfully with tenants, even in difficult situations.
Keep a strong legal advisor to navigate compliance challenges.
Be resourceful—help owners connect with lenders, brokers, and contractors.
Keep owners informed and remind them that things often get worse before they get better!
This project reinforced why I love what I do—turning struggling properties into thriving investments. If you’re facing similar challenges with your property, let’s talk!
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