Vacant and derelict commercial properties negatively impact surrounding businesses and the local community by detracting from streetscapes and discouraging investment. Therefore, local landlords are important stakeholders in encouraging revitalization. The reasons for commercial vacancies and dereliction are influenced by a set of complex factors, which must be better understood to create proactive landlord engagement strategies. This research explores the causes of landlord absenteeism along the Ward 3 section of Hamilton’s Barton Street, quantifies the extent of the issue, and analyses the strategies currently in place to address vacancies. Best practise examples from outside Hamilton are used to evaluate possible additional strategies to engage landowners in property maintenance.