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Midterm rentals are often treated as a fallback when short-term bookings soften. In reality, they operate on a completely different demand cycle, sales process, and operational model. In this episode of CircuitCast – AI Connect, Vivian Yip shares how insurance housing, corporate displacement, and extended stays actually function behind the scenes. Drawing from her experience managing local portfolios through Hestia 360 and operating a nationwide B2B inventory platform through Crew Homes, Vivian explains why many hosts struggle when they simply stretch short-term tactics across longer calendars. You’ll hear how insurance claims trigger immediate housing needs, why families prioritize location and livability over amenities, and how inspection standards borrowed from legacy corporate housing reduce risk for both guests and owners. Vivian also explains the education gap she sees in the market, particularly among owners with one-to-three bedroom homes facing declining short-term demand. Operationally, the conversation highlights calendar control, rate approvals, deposit structures, and why instant booking requires more backend safeguards in longer stays. The discussion closes with a practical look at AI, not as a buzzword, but as a way to scale education, reduce repetitive advisory work, and improve response consistency without adding headcount. This episode is relevant for hospitality leaders evaluating revenue stability, insurance-driven demand, and how AI-enabled systems can support leaner operations. CircuitCast – AI Connect explores how experienced operators are modernizing hospitality operations with practical systems, automation, and AI. Chapters: 00:01 Midterm Rentals and Vivian Yip’s Background 00:59 From Corporate Housing to Furnished Rentals 03:24 Automation, Travel, and Time Freedom 05:08 Day-to-Day Operations and Team Structure 06:17 Coaching, Property Management, and Crew Homes 07:56 Insurance Housing and Inventory Strategy 09:48 Calendar Control and Old-School Deal Flow 10:51 Quality Standards and Property Inspections 13:07 Insurance Client Journey Explained 15:45 B2C vs B2B Housing Channels 16:47 Education Gaps in Midterm Rentals 19:24 Training Hosts to Transition from Short-Term 21:12 Industry Trends and Market Pressure 22:15 Risk, Deposits, and Insurance Backstops 24:11 AI Agents and Scaling Expertise