I’m about to tell you about a deal that could have easily fallen apart, but instead turned into a $200k profit after a lengthy eviction process. This one came from Massachusetts, a state where the eviction laws are not in the landlord's favor. When the lead came in, it was from a brother who inherited a house from his mom. The brother and his son had been living in the house, free of charge, for years, and were gaming the system. The brother was fed up and needed to sell, but there was a significant issue. His brother (the squatter) wasn’t going to leave the property without a fight.

I showed up to the house with my acquisition guy, and things quickly got hostile. The nephew, who had been living there, was livid and started yelling at us to leave. This was the kind of situation where most people would turn around and walk away, but not us. We locked the property up for $240k knowing full well that we were in for a lengthy eviction process.

Massachusetts is one of the most tenant-friendly states, meaning that evictions take time—sometimes a lot of time. We figured it would take six months at least. In the end, it took us a full nine months to evict them.

But that’s not all. We also offered the squatter $10,000 for cash-for-keys, but they rejected it. They came back demanding $30,000, but we knew they weren’t going to accept anything. So, we decided to ride it out and go through the legal process. It was a long and expensive journey, but eventually, we won the court battle and were able to move them out.

After they were gone, we cleaned up the house and decided to list it as-is instead of flipping it. It turned out to be the right decision because we got an all-cash offer pretty quickly.

Once all was said and done, we netted $200k in profit. We managed to bring the property down in price, overcome objections, and navigate the eviction battle, and in the end, it paid off.

The key takeaway here is that if you’re a true cash buyer who can work with private lenders, you can survive long, drawn-out processes like this. Not every investor is willing to take on properties with these kinds of challenges, but if you can make it work, the rewards are huge. Many of our competitors would have walked away, leaving us with the upper hand.

If you have the right mindset and the right resources, properties that others shy away from can become some of your best deals.

Have you ever dealt with a property that took months to resolve? What was the longest eviction or difficult situation you’ve had to navigate?