How a 3-Year Real Estate Nightmare Turned into a $300k Profit

[Jeremy Beland]

In August 2020, I took on what seemed like a great deal—a three-family property in Manchester. The seller was a terminally ill man who needed cash quickly to support his family before he passed. The lead came through one of our absentee equity mailing lists, and after meeting with him, we locked up the deal. At the time, the price was a bit high for us, but I was eager to take another property down for myself after years of wholesaling for other investors. With private lending secured, I bought the property, excited to add another rental to my portfolio.

What I didn’t expect was just how much of a nightmare this property would turn into.

After closing, we began the renovation. The house needed more work than I initially thought—especially when we discovered the entire plumbing system had to be replaced from top to bottom. Once the renovation was complete, I started searching for a property management company, as I don’t manage my own properties. I vetted a few companies and hired one that seemed like the best fit.

This is where the real trouble began.

The first tenant they placed fell behind on rent by the second month. After a series of delays, they were eventually evicted. The second tenant wasn’t any better. Within two months, they were causing disturbances, fighting with neighbors, and creating an unsafe environment for other tenants. Another eviction followed. The third tenant just disappeared one day, leaving all their belongings behind and causing more headaches.

At this point, I had already gone through two evictions and was starting to lose faith in the property manager. So, I switched to a second company. Unfortunately, this change didn’t help. It was around the time of COVID, making it incredibly hard to find reliable tenants. This new property management company was just as ineffective, and for nearly two years, I struggled with bad tenants, constant repairs, and growing losses. By the end of the second year, the property still wasn’t cash flowing, and the situation felt hopeless.

Finally, I decided to switch to a third property management company. This time, things started to improve. They found solid tenants and stabilized the property. But the damage was done—I had already gone through three management companies, three evictions, and a lot of lost rent and legal fees. It wasn’t until 2023 that the property finally began to cash flow.

Then came an opportunity to sell the property in August 2023. After everything I’d been through, I decided to sell. Despite all the headaches, I managed to sell it for a $300,000 profit.

So what did I learn? First, not all property management companies are created equal. No matter how well you vet them, sometimes you won’t know how good they are until it’s too late. Second, real estate can be incredibly forgiving, even when things go horribly wrong. I lost tens of thousands in missed rent, eviction fees, and attorney costs, but in the end, I still made a significant profit.

Would I do it again? Absolutely—but with better property management from the start. Real estate is a long game, and as this experience shows, persistence pays off, even when things don’t go according to plan.