This paper describes work directed toward creating community-supported positive youth development interventions that draw on a developmental intervention science outreach research approach. With respect to developmental interventions, this approach focuses on creating evidence-based longitudinal change intervention strategies for promoting long-term developmental change. The paper describes three broad challenges (theoretical, methodological, and meta-theoretical) that the authors faced in their efforts to develop and implement community-supported intervention programs built on this approach. The authors describe first the theoretical challenges they addressed in developing the conceptual framework for their community-supported intervention; second, the challenge of developing and refining a methodological framework for evaluating positive youth development interventions in “real-world” settings; and third, the meta-theoretical challenges that arose in the context of implementing community-supported positive development programs.