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As society and technology change the way public transit systems are perceived, contemporary professionals need to be equipped with the skills to manage transportation systems to keep up with modern demands and challenges. Information Communication Technologies and data ubiquity represent great potential advances in transport systems; however, the challenge of transferring the knowledge from research and academia remains a significant barrier. This paper contributes to the literature in two ways: it serves as a benchmark for the challenges in transit systems planning education today, and it is a reference guide for future educators to find resources to create and refine effective educational programs in this area. A case study of a sample teaching module for transit systems planning in the Greater Toronto Area is presented with guidelines to teach (1) models of data-driven flexible transit services; (2) technologies to integrate and visualize user and systems data; and (3) methodologies to evaluate demand for such services at a societal level. [ABSTRACT FROM AUTHOR]