This paper explores different building maintenance strategies in commercial buildings in Sydney, Australia, focusing on corrective maintenance (CM) and preventive maintenance (PM). While CM involves rectifying issues after they occur, PM aims to enhance productivity by anticipating potential issues. Although PM seems more logical, the decision to implement this type of maintenance strategy are typically made based on item reliability, failure frequency, and downtime cost, commonly found in manufacturing facilities or critical environments. However, as found in the selected/surveyed commercial real estate buildings, CM was more frequently adopted in aged facilities with older infrastructure, and PM was favoured for buildings without structural deficiencies; however, operating equipment failures were common. However, in many cases, decision makers did not consider the broader effects of downtime beyond direct financial losses, costs associated with customer satisfaction, worker efficiency, rent abatements, and reputation damage. While each building is unique and may require Technical Due Diligence a bespoke maintenance schedule, this study’s insights may help managers select the most appropriate maintenance strategy. Nonetheless, further research is needed to investigate the role of innovative technologies (such as machine learning and artificial intelligence) in enhancing maintenance efficacy and explore the influences of economic shifts, corporate and financial objectives, and the availability of technical resources