This paper presents the results of three interrelated studies concerning the specification and implementation of ambient assisted living (AAL)/Internet of Things (IoT)/sensor-based infrastructures, to support resident wellness and person-centered care delivery, in a residential care context. Overall, the paper reports on the emerging wellness management concept and IoT solution. The three studies adopt a stakeholder evaluation approach to requirements elicitation and solution design. Human factors research combines several qualitative human–machine interaction (HMI) design frameworks/methods, including realist ethnography, process mapping, persona-based design, and participatory design. Software development activities are underpinned by SCRUM/AGILE frameworks. Three structuring principles underpin the resident’s lived experience and the proposed ‘sensing’ framework. This includes (1) resident wellness, (2) the resident’s environment (i.e., room and broader social spaces which constitute ‘home’ for the resident), and (3) care delivery. The promotion of resident wellness, autonomy, quality of life and social participation depends on adequate monitoring and evaluation of information pertaining to (1), (2) and (3). Furthermore, the application of ambient assisted living technology in a residential setting depends on a clear definition of related care delivery processes and allied social and interpersonal communications. It is argued that independence (and quality of life for older adults) is linked to technology that enables interdependence, and specifically technology that supports social communication between key roles including residents, caregivers, and family members.