Patient self-management programs and information systems that support them can improve the quality of healthcare. Flaws in user experience reduce the willingness of patients to adopt such systems. To explore how emerging technology such as rich Internet applications can be used to address the usability issues of personal health information systems, we developed a health self-management application that is based on an open-source framework. In this work we present the architecture of the system, discuss the issues we faced and lessons we learned while developing it. This work can help researchers and practitioners in evaluating approaches towards developing new generation of personal health solutions. Furthermore, this work serves as a basis for implementing a feature-rich system that can improve chronic disease self-management.