Public school facilities have been underfunded and experienced deferred maintenance, creating deteriorating and aging facilities. This study sought to fill a scholarly research gap and inform school leaders of conditions impacting the willingness of local communities to address school facility needs. Using semi-structured interviews, this qualitative, multiple-case study explored the experiences and perceptions of current and former school superintendents and current and former school board members from two low-wealth, rural school districts in North Carolina on conditions that affected the willingness of local communities to address school facility needs. Findings indicated that community trust positively impacted the willingness to address facility needs. At the same time, resistance to increased taxes to support school bonds and contentment with their current schools due to tradition and family history hindered efforts to improve facilities. Implications suggest the importance of building trust between the school district and its community through frequent communication. Additionally, creative funding strategies that do not raise taxes are essential to maintain community support. Finally, this study also suggests that the state’s reliance on local governments for most facility funding burdens low-wealth counties, exacerbating their facility challenges.