Cassondra Liles has spent 25 years helping buyers, sellers, and investors make strategic real estate decisions. As the broker of The Key Team and the author of Real Life Monopoly, she brings a goals-first, data-driven approach to short-term rental investing that cuts through the noise and gets straight to what actually works. Her own vacation rental income portfolio, built across the mountains and the coast of North Carolina, grew from an accidental first purchase near East Carolina University that became one of her best-performing assets. In this episode, Lynell sits down with Cassondra to unpack what separates profitable short-term rental investors from those who struggle to sustain their portfolios. The conversation covers how to evaluate market saturation before you commit, which investment property numbers matter most before you buy, why the hybrid rental model is becoming an increasingly smart ownership strategy, and why so many investors go wrong by leading with emotion instead of data. Cassondra also shares the story behind Real Life Monopoly and the online course she's building to help first-time investors get it right from the start. This episode is sponsored by Streamline Summit.