Every day we face numerous lifestyle decisions, some dictated by habits and some more conscious, which may or may not promote sustainable living. Aided by digital technology, sustainable behaviors can diffuse within social groups and inclusive communities. This paper outlines a longitudinal experimental study of social influence in behavioral changes toward sustainability, in the context of smart residential homes. Participants are residing in the housing on campus referred to as KTH Live-In Lab, whose behaviors are observed w.r.t. key lifestyle choices, such as food, resources, mobility, consumption, and environmental citizenship. The focus is on the preparatory phase of the case study and the challenges and limitations encountered during its setup. In particular, this work proposes a definition of sustainability indicators for environmentally significant behaviors, and hypothesizes that, through digitalization of a household into a social network of interacting tenants, sustainable living can be promoted. Preliminary results confirm the feasibility of the proposed experimental methodology.