Emerging transportation services, whose development and adoption have been enabled by information and communication technology, are largely transforming people’s travel and activity patterns. This study investigates the emerging transportation trends and how they transform travel-related decision-making in the population at large through the application of a unique longitudinal approach. As part of this project, a second wave of data collection in 2018 was built with a rotating panel structure as a continuation of the research efforts that started with the collection of the 2015 California Millennials Dataset. This report focuses on the analyses of the data collected in this project, in particular on the differences in attitudes towards transportation and the environment among different generational groups, the adoption and use of shared mobility services, and their relationship with vehicle ownership, the interest in the adoption of alternative fuel vehicles, and the interest in the future adoption of connected and automated vehicles. Due to the small number of respondents who participated in both surveys, for the purposes of the analyses contained in this report, we treated the data as repeated cross-sectional and analyzed the data from each survey separately. The study helps researchers evaluate the complex relationship between observed/latent characteristics and individual travel-related choices and decision-making. The study highlights attitudinal and mode-choice differences across generations. It explores the factors impacting current adoption of and future interest in new transportation technology including alternative fuel vehicles, automated vehicles and shared mobility. Divergent consumer segments are witnessed within each of these markets, with distinctive socio-demographics, latent attitudes, built environment, and level of familiarity with new technologies, which shape the uniqueness of their vehicle ownership, residential location, travel behavior, activity patterns, and lifestyle.