In 2020, an inner-ring suburb of Pittsburgh, Ross Township, made the Money’s Best Places to Live in America, ranking 48th of the top 50. That recognition is in part due to the success of the North Hills School District, to which Ross Township belongs.  But that success was not achieved overnight, and its foundation may be shakier than it seems.  This article, through a twenty-year case study of the North Hills School District, examines the challenges of financially managing a successful public-school district facing the common problem of unpredictable and substantial fluctuations in annual student population. This chronicle has elements of a success story, but it is too soon to evaluate the full effect of the virtually-irreversible decisions that the school district made in this period – the selling of school buildings and the parcels of land on which they sit.  From this study, this paper posits that such a decision, along with the resulting increases in property tax rates, is not a prudent approach to the financial administrative of an otherwise healthy and high-achieving school district.  This is especially so in light of the alternatives for managing unpredictable fluctuations in student population.