Wheelchairs are essential assistive devices that support mobility and independence in both older adults and individuals with disabilities. Although their history dates back to ancient times, modern designs incorporating lightweight materials and foldable structures emerged in the early twentieth century. Today, wheelchairs have diversified into specialized models for sports and caregiving, with electric wheelchairs significantly reducing physical strain and enabling greater social participation. In Japan, public funding and policy initiatives have played a crucial role in wheelchair provision. Since the enactment of the Act on Welfare of Physically Disabled Persons in 1949, various assistive devices have been subsidized to enhance the independence and quality of daily life. The scope of financial support has expanded over time, including the introduction of electric wheelchairs in 1989 and advanced postural support systems in 1990. Despite long-standing public support, the effectiveness of assistive device provisions remains insufficiently analyzed. The research report tracking 1997–2023 trends revealed a decline in manual wheelchair subsidies, largely due to the Long-Term Care Insurance Act promoting rental-based distribution. Electric wheelchair provisions remain relatively stable but show a gradual decline. Understanding these policy trends is key to optimizing future welfare programs. Ensuring the mechanical safety and effectiveness of wheelchairs is crucial for user confidence, injury prevention, and functional optimization. Given that a wheelchair is essentially an extension of the user’s body, mechanical failures can lead to serious injuries, necessitating continuous assessment and improvements in design and materials. Industry standards such as the ISO and JIS help regulate wheelchair durability, but evolving user needs demand ongoing evaluations. For example, excessive force exerted by users with cerebral palsy or stroke-related hemiplegia can lead to wheelchair structural failure, thereby posing risks. Studies on foot and head support have quantified mechanical loads, revealing that foot support forces can reach 134% of body weight, while head support loads during spastic episodes can reach 88.3% of body weight. Beyond safety, the compatibility between wheelchairs and users affects comfort and pressure ulcer risk. While the pressure distribution is widely measured, shear force remains difficult to assess owing to sensor limitations. To address this, researchers have developed thin, flexible shear force sensors that can successfully visualize force variations during posture shifts. Future research should refine measurement techniques to enhance scientific wheelchair-user assessments and ensure optimal adaptation for assistive mobility devices. With the progression of population aging, accidents involving wheelchair use by elderly individuals with cognitive impairments are increasing. In this study, we developed a multisensory alert system to support safe wheelchair operation and training. The system was gradually improved by incorporating sensors on the brakes and foot supports, as well as combining visual, auditory, and vibratory feedback. In the final stage, visual guidance through visual stimuli was also introduced. The system was evaluated with elderly individuals who had cerebrovascular disorders and moderate cognitive impairment, and the results showed a reduction in operational errors and task completion time under the condition combining visual, auditory, and vibratory stimuli. This system is expected to be useful for future clinical applications and for use in home and institutional settings, serving as an effective aid for learning safe wheelchair operation.