Children with medically complex dis/abilities hold sophisticated views on effective school leadership, adapted built environments, inspiring peer solidarity, catalyzing transformational solutions and a possible school-hospital liaison model to support student well-being. Using child-centric collaborative techniques, this ethnodramatic study engaged children with osteogenesis imperfecta (oi), a rare genetic disease, to create a children’s book describing their moral experiences to be disseminated to other children and families. Children living with oi experience ongoing medical interventions and dis/ability that broadly jeopardized the quality of their academic experience relative to their peers. As such, children living with oi offered trenchant insight into what supports and thwarts operationalization of their values and highlights the programs, leadership, services and paradigm shifts they feel that they need to flourish in the academic context.