The safety of road users within road systems has been a burning public health issue since road accident became the highest cause of death in urban areas. This trend has informed a number of studies carried out to critically review the trend in road traffic accidents and road safety approaches with a view to identifying underlying and systemic problems giving way for the high rate of road crashes. This study aims to identify and analyze the inherent problems associated with road usage and specify how roadway elements can best support road users in improving performance. Data were gathered through observational studies of selected road usage scenarios and interviews of road users. A set of human factors methods and Applied Cognitive Work Analysis (ACWA) framework was used to exhaustively examine the human-roadway system interaction for tasks-system constraints and possible human errors. The results showed that constraints and demands faced by road users within the road system determine their safety when navigating the roadways. In particular, advertorial billboards around critical sections of the roadway affect the cognitive workload of road users and ultimately their performance. The analyses also produced Representation Design Requirements (RDR) specifying ways to support road users in decision-making performance through affordances and driving decision aids, which informs the design of training requirements for drivers, intelligent transport systems, roadway signage, vehicle cockpits, roadway layout and other roadway elements. To effectively design roadway systems in improving the safety of road users, sufficient human factors information and concepts can be generated by the results of carefully selected human factors analysis methods integrated into the road system design cycle/process.