Using logistic regression, this study sought to understand the relationship between district characteristics, district finances, levy characteristics, and campaign expenditures with new operating levy outcomes. We found that employee benefits as a percentage of the district's budget were negatively associated with levy outcomes, while salaries were positively associated with levy outcomes, suggesting that voters may be more sensitive to retirement and healthcare benefits than salaries when voting. While campaign spending was related to levy success, types of expenditures were largely insignificant. School district personnel must be cognizant of the local conditions in crafting campaigns and recruiting community stakeholders.