To document an individual's longitudinal construction of risk is a logistically intensive task. To identify a logistically feasible approach, we review existing agent-based experience documentation approaches within the context of a specified risk source - performance of a transportation network. The most promising documentation method, GPS tracking, was then tested in a four month pilot study This study found that while GPS tracking documents an individual's activities in extreme detail, the psychological context of these activities is missing. To contextualize this data, the feasibility of applying three different hedonic psychology research methodologies is assessed. From the perspective offered by this pilot study, it is believed a daily survey documenting the individual's observed key experiences combined with a focused survey qualifying recent GPS documented experience variances shows potential for being a comprehensive and logistically feasible methodology for documenting an individual's longitudinal construction of risk.