In recent years there has been a rapidly increasing intensity of work going into investigating various methods of facilitating assisted living for the benefit of the elderly and those with difficulties in mobility. This chapter describes one such effort which distinguishes itself from the rest by considering and describing a system with true commercial potential and thus significant social impact. Promising efforts in investigating and identifying the requirements for a system of smart monitoring and adaptive lifestyle pattern detection and analysis are described. An initial proposal for a system relying on remote monitoring using persistent communications technology and a centralized data gathering, analysis and decision making is presented. During the initial development stage requirements for sensor placements, efficient sensor data formats and transmission protocols became apparent; unit testing and system validation demanded generation of large amounts of suitable sensor data. Here we also describe a simulator we developed in order to support these requirements; the rationale behind the simulator, its main functions and usage and the positive contribution it has made during the initial stages and the prototyping phases of the above system are explained. Finally a prototype developed in facilitating initial investigations is described and the vision for future developments is articulated.