This study addresses the research gap in understanding practitioner perspectives on evaluating placemaking initiatives, a popular cross-sector process used to enhance community vitality and public spaces. Through interviews with twenty (20) U.S. practitioners, the research identifies wide variations in evaluation requirements, capacity constraints, and challenges linked to complexity, leadership transitions, and data limitations. Despite these barriers, effective evaluation supports learning, advocacy, and funding outcomes. Findings highlight the inherent tension between flexibility and structure in current evaluation practices while underscoring the need for collaborative, systematic, and context-sensitive approaches. This study contributes to broader discussions in cross-sector initiatives.