This paper reports on and discusses recent research into software agent mediated retailing and considers how it may act as a catalyst to the formation of local electronic retail communities. Each member of the e-retail community has their own software agent that acts on their behalf. Their software agent acts as an electronic Personal Sales Assistant (ePSA), interacting with the person and assisting with the selection and purchase of products. We consider issues that arise when each person can express their likes and dislikes for various aspects of the product range to their software agent, both in terms of the software agent's ability to serve them better, and how such preferences may be shared with others in the larger community to help them -and others in the community -make better and more informed choices. The investigations reported use the MAPPA system, an experimental kiosk based e-retail system. MAPPA integrates a software agent based architecture, a novel form of product display and the use of an animated character agent to enhance the user's sense of personalisation. We report on user evaluation studies of the MAPPA system to investigate the effectiveness of the character agent as an interface to the e-retail system using both conventional usability evaluation techniques and eye-tracking technology. We also describe a simulation program that allows us to investigate the dynamics of e-retail community cohesion when a number of different parameters are considered, including the characteristics of the individual community members and the algorithms employed by the software agents to share information. Lastly, we develop and discuss notions of loyalty, trust, reputation and preference, four issues critical to the development and maintenance of the relationships between individual people, their personal software agents, businesses and the larger e-retail connected community. We propose these issues as "supra-functional" criteria for human-computer interaction design in this area.