Because homelessness assistance programs are designed to help families, it is important for policymakers and practitioners to understand how families experiencing homelessness make housing decisions, particularly when they decide not to use available services. This study explores those decisions using in-depth qualitative interviews with 80 families recruited in shelters across four sites approximately six months after they were assigned to one of four conditions (permanent housing subsidies, project-based transitional housing, community-based rapid re-housing, or usual care). Familiar neighborhoods near children's schools, transportation, family and friends, and stability were important to families across conditions. Program restrictions on eligibility constrained family choices. Subsidized housing was the most desired intervention, and families leased up at higher rates than in other studies of poor families. Respondents were least comfortable in and most likely to leave transitional housing. Uncertainty associated with community-based rapid re-housing generated considerable anxiety. Across interventions, many families had to make unhappy compromises, often leading to further moves. Policy recommendations are offered.