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Mike Morawski sits down with Kenny Bedwell of STR Insights to break down STRs as an operator business, not a passive rental. Kenny shares how he started with a duplex house hack, then scaled into vacation-market, amenity-heavy properties. You will hear real numbers, how regulation and community sentiment shape risk, and why underwriting must start with revenue and operating costs instead of interest rate stress. You will learn: How a duplex house hack produced about three times long term rent through Airbnb How parent child listings turn small units into whole-building group bookings for two times peak season revenue How to evaluate regulation, deed restrictions, and community sentiment before you buy How Kenny targets returns by budgeting for furnishings and amenities, not only the down payment Topic Sections: Intentional goals and heading into 2026 with a market shift Kenny Bedwell background from Citibank data analyst to STR operator The duplex house hack and the 3x rent Airbnb lesson Parent child listings and peak-season group booking math Diversification and portfolio protection after Hurricane Helen delays Micro resort design: amenities, guest avatar, and buildout budgets Deal underwriting: revenue first, debt service second Regulation strategy: why no-rules markets bring the most risk Where the STR industry is heading: average decline, top 10% rising