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One of the fascinating things about real estate is that you can make mistakes and still walk away with a profit. That does not mean the mistakes are worth repeating. In this episode of Chat with Chatto, Stephen reflects on three landlord decisions he made over 25 years that he would never repeat, even though they ended up making money. This is not a dramatic bankruptcy story. It is a practical breakdown of how real estate can sometimes cover your errors, and why that safety net can create dangerous habits. Chatto shares real examples from his own investing journey, including buying in the wrong neighborhood, purchasing a rooming house, and making tenant exceptions that affected structure and discipline. While appreciation and timing helped soften the impact, the lessons were costly in stress, time, and management headaches. In this video, you will learn: Why location mistakes can still hurt even if you profit later The hidden operational challenges of rooming houses How making tenant exceptions can damage long term stability Why waiving late fees and bending rules creates bigger issues The difference between getting lucky and making smart decisions If you are building a rental portfolio, this conversation will help you avoid preventable mistakes and protect both your cash flow and your sanity. #landlord #realestateinvesting #rentalproperty #propertymanagement #cashflow #landlordlife #realestateeducation #propertyinvestor #wealthbuilding #rentalbusiness #investingsmart