Road networks are critical infrastructures within any region and it is imperative to maintain their conditions for safe and effective movement of goods and services. Road Management, therefore, plays a key role to ensure consistent efficient operation. However, significant resources are required to perform necessary maintenance activities to achieve and maintain high levels of service. Pavement maintenance can typically be very expensive and decisions are needed concerning planning and prioritizing interventions. Data are key towards enabling adequate maintenance planning but in many instances, there is limited available information especially in small or under-resourced urban road authorities. This study develops a roadmap to help these authorities by using flexible data analysis and deep learning computational systems to highlight important factors within road networks, which are used to construct models that can help predict future intervention timelines. A case study in Palermo, Italy was successfully developed to demonstrate how the techniques could be applied to perform appropriate feature selection and prediction models based on limited data sources. The workflow provides a pathway towards more effective pavement maintenance management practices using techniques that can be readily adapted based on different environments. This takes another step towards automating these practices within the pavement management system.