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We examine rental landlords’ decisions to buy and sell investment properties. We use the results of a new survey of owners of rental properties in nine major US cities, focusing on a subset of rental investors who own properties themselves, where we ask questions about their demographic and economic backgrounds, rental portfolios, and business management practices, and questions about their interest in acquiring new investments and plans to sell properties currently in their portfolio. We use these data to specify a series of regressions examining the factors that shape owners’ decisions to grow or shrink their businesses. First, we examine whether financial factors affect acquisition and disposition decisions. In this category, we include a variety of measures, including rents, external shocks, the owner’s reliance on rental income, debt, and portfolio characteristics. Second, we examine the impact of the owner’s personal characteristics—including age, gender, race, and ownership length—on investment behavior. Finally, we examine the influence of operating experience on future investment decisions, including interactions, vacancies, evictions, property investment, and business impacts from COVID-19 and other external events. Our analysis contributes to a growing body of research on the businesses of small landlords and their impact on the housing system.