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Designing healthcare systems for the elderly is a challenging endeavour. Telehealth systems are gaining popularity among elderly users, but such applications are mostly doctor-centric and are predominantly used for managing and/or treating diseases instead of preventing them. They do little to motivate patients to change their lifestyle and proactively manage their health. To address these shortcomings, we propose a web-based telehealth system, which uses Web 2.0 technologies in order to add social support and user defined content. In this study, we determine the functional and interface requirements of the system by conducting open individual semi-structured interviews with eight elderly people of age range 60 to 87. A paper prototype and three interfaces of existing Web 2.0 health applications were used to determine the optimum user interface design of the system. A qualitative content analysis was used to evaluate the responses. Overall, the respondents were positive about the idea of using the web to manage their healthcare from home and made several suggestions such as including applications to manage their diet, physiotherapy exercises to improve their health conditions and simple network games to reduce loneliness.