AIM (Assess, Identify, Make it happen) is a community-engaged, data-driven, strategic planning process for school districts to develop and implement comprehensive health and wellness plans (CHWPs) aligned with the Whole School, Whole Community, Whole Child (WSCC) model. AIM was facilitated in 21 rural school districts and an 81-item survey was administered to participants completing this process (n = 236). Those surveyed indicated that the benefits of AIM were more pronounced than challenges. Top benefits included developing a shared commitment and long-term mindset to promote health and wellness in schools. Top challenges included fitting AIM into already busy schedules and getting buy-in from all task force members. The most common health problems prioritized in district CHWPs were poor mental health and alcohol tobacco and other drugs. These results support the effectiveness of AIM as a method for developing community-engaged, data-driven CHWPs with rural school districts. Future efforts to create school plans to promote health should account for the benefits and challenges noted in this work. Furthermore, approaches designed for rural and historically under-resourced schools are necessary to promote the equitable implementation of the WSCC model.