This paper contributes to the current discourse on practice-based research in HCI paying particular attention to the overall temporal and situational conditions which frame an R&D project. We present a Living Lab study situated in an arbitrary neighborhood of a German city which develops ICT support to foster informal help and social interaction with a special, but not exclusive, focus on elderly tenants. We demonstrate that practice-based, long-term research in a city quarter goes beyond those challenges already described in the current Living Lab and PD literature. The long-term study's positioning in a real-world context is contoured not only by a high diversity of stakeholders and their individual interests and motivation for participation but also by their individual skill sets and learning needs. These distinct and often contradictive perspectives have to be permanently counterbalanced. Thus attention has to be focused on how related strategies and decisions impact on the design of the project as well as on the final ICT product. To enable all tenants, irrespective of age and technical skill, to participate in a long-term ICT-based community development project, we applied the format of 'experience-based PD workshops' to foster confidence in ICT usage and encourage the competency of the elderly and non-tech-savvy tenants.