Healthcare strategic sustainability seeks to integrate in a cost effective manner sustainable development and design practices with health care facilities that are holistic places of healing for patients; and a safe, efficient, and effective environment for staff. This study focused on six United States Army military healthcare facilities involving conversion from inpatient to outpatient facilities. Data was collected in an intensive interview process from twenty-nine participants representing three stakeholder categories: planners (design and construction), operators (facility management and information technology), and users (clinical staff). The specific research questions addressed what design/building changes were made to accommodate the change from an in-patient to an outpatient care business model; and which existing design/building elements generated significant constraints or benefits when implementing the desired new design concept? The research also explored whether any desired design/building changes were not made, and why; and the extent to which social (quality of care and/or quality of life), economic (cost), or environmental (adaptable and sustainable) factors were considered? The findings confirm the impact of certain design elements on the conversion and adaptability of hospitals; and suggest the need to educate organizations on which design elements to invest in that not only meet cost and environmental quality goals, but also contribute positively to staff quality of life.