The quest for user friendly systems that fit into an organizational reality and yet stay competitive on a very crowded marketplace is a challenge. This report covers the setup of an eHealth project that faces challenges in all these areas, not least in the intersections between them. We discuss these challenges in the context of a research and development project, FRONT-VL, which is in its start-up phase, giving samples of problems and opportunities. The purpose of the paper is to problematize eHealth development and to provide initial insight into the planning and conduct of such projects.