Successful implementation of Housing First requires a good supply of affordable housing. Since 2002, the Canadian Mental Health Association, Ottawa Branch, has purchased 40 condominium units in regular buildings scattered across Ottawa, Canada, to rent to their clients with severe mental illnesses who have a history of homelessness. Seeking to share their experience of this approach that creates affordable housing for Housing First tenants, researchers conducted a case study of the program, documenting its implementation and client outcomes. Thirteen tenants and 24 key informants (staff, management, board members, property managers, and funders) participated. Tenants reported housing stability, improved mental and physical health, decreased substance use, and community integration. Key informants echoed these positive outcomes. Participants also identified program challenges, including aging clients, loneliness, experiences of exclusion, and a vulnerability to home takeovers. At the program-level, challenges included unanticipated program costs, heavy case manager workloads, managing repairs, some eviction cases, and the high prices of condos in central, accessible areas.