Given the unique challenges faced by manual wheelchair users, improving methods to accurately measure and enhance their participation in community life is critical. This study explores a comprehensive method to evaluate the real-world community mobility and participation of manual wheelchair users by combining GPS mobility tracking, heart rate, and activity journals. Collecting qualitative and quantitative measures such as the life space assessment, wheelchair user confidence scale, and physical performance tests alongside GPS mobility tracking from ten manual wheelchair users provided insight into the complex relationship between physical, psychological, and social factors that can impact their daily community mobility and participation. This study found significant, strong correlations between the recorded journal time outside of the home and the GPS mean daily heart rate (r = −0.750, p = 0.032) as well as between the upper limb strength assessments with cardiovascular assessments, physiological confidence, and GPS participation indicators (0.732 < r < 0.884, 0.002 < p < 0.039). This method of manual wheelchair user assessment reveals the complex relationships between different aspects of mobility and participation. It provides a means of enhancing the ability of rehabilitation specialists to focus rehabilitation programs toward the areas that will help manual wheelchair users improve their quality of life.