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Writer's pictureDan Caradonna

Lessons in Land: Overcoming Challenges for a Big Payoff

I recently closed on another funding deal, and this one was one of the toughest I’ve ever had to navigate. The property involved eight different sellers, all siblings, who each had to sign off on the deal. If that wasn’t challenging enough, we also had to negotiate and secure an easement just to gain access to the property. Despite all the hurdles, we purchased the property for $85k and eventually sold it for $235k—a significant win.


Here are the lessons I took away from this complicated yet highly rewarding deal:


1. The more problems, the more profit: In real estate, when you see a property with multiple issues or obstacles, that’s often a sign of opportunity. Many investors will pass on these kinds of deals, which leaves a smaller playing field for those willing to take on the challenge. While properties with fewer complications are often easier to flip, the ones with problems can yield higher returns. This deal almost didn’t happen because of all the complications, but by sticking with it and overcoming each hurdle, we turned it into a six-figure profit. Don’t be afraid to dive into a complex situation—it could lead to your next big win.


2. Surround yourself with good people: Success in real estate is rarely a solo effort, especially with complex deals. I was fortunate to work with an experienced investor who was thorough and didn’t cut corners. We had collaborated on multiple deals before, and knowing the quality of his work gave me the confidence to press forward, even when the deal got complicated. This is a crucial point—having a reliable team or partner makes navigating tricky deals much easier. Choose your partners wisely, because having the right people in your corner can be the difference between success and failure.


3. Partner up if you’re newer: If you’re still gaining experience, complicated deals like this can feel overwhelming. When you're new to the business, it’s easy to miss key details or underestimate the complexities of a property. That’s why partnering with a more seasoned investor can be invaluable. Sure, you may have to share some of the profit, but the experience and guidance will help you avoid costly mistakes. In this case, collaborating allowed us to handle the intricacies of the deal without missing a beat, ensuring a profitable outcome.


Conclusion:

This deal was a clear reminder that challenging properties can lead to the biggest rewards. It’s easy to shy away from properties with complications, but those are often where the greatest opportunities lie. By surrounding yourself with experienced partners, taking on challenges, and leveraging your problem-solving skills, you can turn difficult deals into some of the most profitable investments in your portfolio.


Thank you,

Dan Caradonna

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