How I'm Analyzing Deals in 2026

How I'm Analyzing Deals in 2026

July 16, 2026 · 30 min · Episode 177

About this episode

Kenny Bedwell discusses strategies for analyzing short-term rental deals in 2026, emphasizing market understanding and property quality.

To analyze short-term rental (STR) deals in 2026, it is essential to recognize the professionalization of the industry, which requires higher standards for design, amenities, and overall property quality. Key strategies for effective deal analysis include: Move Beyond Geographic Analysis: Analyzing revenue solely based on a property's immediate geographic radius or comparable listings is often short-sighted and disappointing. Prioritize Market Understanding: Start by analyzing the market first: determine the primary traffic drivers, identify the guest avatar, and understand what guests are willing to pay for. Utilize Buy Boxes: Predetermine the characteristics of a successful property—such as size, design, amenities, and "look and feel"—before evaluating individual deals. Define "Deals" vs. "Properties": A property only becomes a "deal" when it meets your specific return on investment (ROI) goals. Establish a Conservative Baseline: When market data is limited, underwrite based on a conservative baseline of what current properties are generating. Do not project significantly higher returns without proven data, though acknowledging that superior quality and amenities can lead to…

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