Computerized information systems are used in all contemporary industries and have been applied to track maintenance information and history. To a lesser extent, such information systems have also been used to predict or simulate maintenance decisions and actions. This work details two models, a population data analysis, and a system infrastructure, to aid operations and maintenance managers with the difficult resource allocation decisions they face in the field. The first model addresses the consideration of component dependency for series network connections using a Markov Decision Process model and solution algorithm. The second model addresses the prioritization of maintenance activities for a fleet of equipment using an Analytical Hierarchy Process and solution algorithm. A recurrent event data analysis is performed for a population data set. The final element is the information system architecture linking these two models to a marketing information system in order to provide quotations for maintenance services. The specific industry of interest is the electrical power equipment industry with a focus on circuit breaker maintenance decision actions and priorities and the development of quotations for repair and replacement services. This dissertation is arranged in a three paper format in which each topic is self contained to one chapter of this document.