This study presents findings from a pilot evaluation of user experiences with Tracy, an integrated contact tracing and health monitoring system comprising an IoT-based wearable device and a mobile application. The wearable tracks physiological indicators (e.g., body temperature, heart rate), while the app facilitates location-based contact tracing and movement analysis. 128 participants from six geopolitical zones used the system over a period of five months and provided feedback on their experiences, including their willingness for continued use. Data preprocessing (cleaning, tokenization and lemmatization), thematic extraction using Latent Dirichlet Allocation, and rule-based sentiment analysis were employed to analyze feedback. Results show strong positive perceptions of Usability (90%) and Engagement/Interest (80%), whereas Performance (14.3%) and Content/Features (9.1%) indicated areas for improvement. The study provides actionable insights for refining digital health tools in resource-conscious settings while balancing functionality with user experience.