Using in-depth interview data from families and service providers, we examine the success of the Creating Moves to Opportunity (CMTO) program in Seattle, focusing on how it reduced many of the learning, compliance, and psychological costs of using housing vouchers so that participants could expand their residential choices. CMTO’s approach of combining information and flexible financial resources with personalized high-quality assistance bolstered participants’ confidence, agency, and optimism for their housing searches in high-opportunity neighborhoods. Accessible, collaborative, pertinent communication from program staff was central to addressing both the psychological costs of the federal Housing Choice Voucher program and families’ experiences in housing and social services. These results provide evidence to inform housing policy as well as to enrich broader scholarship on program take-up, implementation research, and the role of Navigators and service quality in addressing administrative burdens low-income families face while using other social programs.