This paper discusses issues in developing descriptive and predictive models of information flow and expertise development in complex task environments.  These concepts are of importance in a variety of contexts, including task coordination, team performance, and learning and training environments.  Acquisition of expertise at individual and group / team levels has been an area of substantial study for over a century, but relatively few models have demonstrated robust implementation when moving from lab contexts to “cognition in the wild”.   By contrast, a number of computer game concepts have been used to simulate expertise development in a non-deterministic way during dynamic game play.  Based on general discussions of “player stats,” several approaches exist to consider both non-rationalities, and domains of relative effectiveness, to describe character development and coordination between members of teams.  This paper examines some of these concepts, as well as areas of personality research that could be used to plausibly model development and coordination of individual and team-level knowledge structures in complex settings.