Taylor sits down with Jacob — a Bay Area tech professional turned short-term rental investor — to unpack the real story behind taking a “big swing” on a remote, high-risk property… and having it pay off. Jacob shares how growing up in San Francisco made real estate feel impossible, why a single long-distance rental accidentally sparked his investing journey, and what finally pushed him from long-term rentals into STRs. Then it gets real: an $800K lakefront property in Northern Michigan, a mas...