This chapter takes a look at the task of creating multimedia authoring tools for the amateur media creator, and the problems unique to the undertaking. It argues that a deep understanding of both the media creation process, together with insight into the precise nature of the relative strengths of computers and users, given the domain of application, is needed before this gap can be bridged by software technology. These issues are further demonstrated within the context of a novel media collection environment, including a real- world example of an occasion filmed in order to automatically create two movies of distinctly different styles. The authors hope that such tools will enable amateur videographers to produce technically polished and aesthetically effective media, regardless of their level of expertise.