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The Chicago-Cook County 2Gen Economic Mobility Demonstration provided family-centered coaching and support to low-income households with children and teenagers participating in the federal Housing Choice Voucher (HCV) programs administered by the Chicago Housing Authority and the Housing Authority of Cook County. The demonstration reached families in a diverse range of neighborhoods, from middle-class suburbs to high-poverty urban areas, and provided services to low-income families living in these neighborhoods. We draw on this variation in household location to understand how support services interact with neighborhood context to shape the well-being of youth and their path to adulthood. In collaboration with local community partners, we designed a qualitative, longitudinal study of adults and youth that we started fielding in summer of 2022. The housing policy portion of the study focused on residential decision-making and the factors that lead families to stay in or move away from “opportunity areas,” or the kinds of low-poverty, resource-rich neighborhoods that have historically high rates of upward mobility among youth. We find that family’s sense of belonging in the neighborhood, combined with a lack of race or class-based antagonisms from landlords or neighbors, support families staying in place. However, families who do experience racist or classist treatment and other forms of discrimination may also stay, if they find sustained support from schools, social networks, or other sources in the community. On the moving side, a forced move stemming from a circumstance outside of a family’s control, or an experience of race or class-based antagonism from landlords or neighbors that is not offset by other supportive neighbors, resulted in a family moving out of an opportunity neighborhood. These findings can be used to tailor existing housing mobility programs to support sustained stays in opportunity areas. They also emphasize the importance of fostering community connections in 2Gen programs. The youth portion of our study explored how young people envision their futures and the role of neighborhoods and 2Gen programmatic services in supporting those goals. We identified three types of “identity projects,” or hobbies, activities, and skills that youth discover about themselves as they are growing up and that shape how they think about their future. These identity projects have varying degrees of connection to youth’s experience with family, school, and community that are helpful as we evaluate the indirect impact of parent’s participation in the 2Gen Demonstration on young people’s path to adulthood. We note the role of school extracurricular programming and opportunities for community engagement in fostering youth development. We also consider the influence of parental career growth, fostered through the 2Gen demonstration, on how youth reflect on their own futures. Together our studies provide actionable insights and point to specific ways to build upon housing policies to support low-income youth development.