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Understanding how school selection processes sort children into schools throughout a metropolitan area is critical given the large disparities in educational opportunity among cities and surrounding suburbs. This paper uses in-depth interviews from a diverse group of black and white families across a range income levels living in the Cleveland metropolitan area. We investigate how families view their school choices, what their ideal educational arrangement is, and what constraints they face in achieving this ideal. Additionally, we explore how these preferences and constraints are shaped by, and in turn shape, patterns of racial, economic, and educational inequality across the metro area. We find that most families’ ideal scenario is to live in a neighborhood that affords them access to a local school that meets their expectations, something we call the “package deal.” Some families are able to easily attain this goal, while other face constraints so severe they must decouple residential and school decisions. In this paper, we focus on families in between these two extremes—those who desire the “package deal” but face significant constraints. We examine who is and is not able to access this ideal scenario, unpacking constraints families face in this process. We find that access the “package deal” falls along racial lines. In this way, our study describes one mechanism for how racial inequalities in educational opportunities get reproduced.