Objective: Recent evaluation of a transitional living centre program showed improved instrumental activities of daily living (iADL) at discharge, but without general gains in role resumption. Accordingly, we examined relationships between self-reported difficulty with iADLs and the associated roles of social integration, housework, meal preparation, and finances. Method: Fifty patients underwent (M = 29.61, SD = 17.29) weeks of treatment consisting of individualized training in life skills and cognitive remediation strategies, group therapies, and family education. Patients completed 2 surveys at admission, discharge, and after 7–8 months: the Rehabilitation of Activities of Daily Living Scale-II (RADLs) and the Community Integration Questionnaire (CIQ). Results: We first tested whether self-reported skill levels related to roles held at the same program stage. At admission, more self-reported social disability predicted less social integration. As the level of difficulty increased 1 unit in meal preparation (follow-up) and in organizing personal finances (discharge/follow-up), the odds of an independent role (“yourself” vs. “someone else”) decreased by at least .43 (p ≤ .05). We then tested for relationships between independence in roles at discharge or follow-up (the outcome) and the skills at discharge while controlling for the skills at admission. Skill level significantly predicted independence in managing household finances and housework at discharge, but not meal preparation or social integration. Conclusion: Skill difficulties predicted independence in corresponding roles, although not uniformly across program stages. Models controlling for pre-treatment skill suggest that skill changes arising during the Program predicted roles at discharge. Still, not surprisingly, skill at admission had an overarching influence.