In urban areas like New York City, school choice systems intend to break the connection between residential segregation and schooling by allowing students to attend schools outside their neighborhoods. If successful, school choice could benefit historically underserved students. However, recent research suggests that achievement gaps and segregation persist in certain school choice districts. This study measures family preferences using (1) the characteristics of families' chosen schools and (2) an experiment that assesses how much families value three school characteristics. In the survey, families ranked and rated their likelihood of applying to sets of hypothetical schools. These schools varied only by safety, academic performance, and racial composition. By randomly varying these limited factors, the experiment can evaluate how much families value each of them. persist in certain school choice districts. Policymakers need to understand what barriers exist in school choice systems that prevent students from receiving their intended benefits and which policy responses can break down those barriers. This study shows that middle school diversity reduces information gaps in high school, suggesting that early policy interventions may lead to long-lasting improvements.