Since 1995, we have been developing a series of highly autonomous wheelchair prototypes (TAO-1 through TAO-7) based on New AI (Behavior-based AI) and Evolutionary Robotics principles [1][2][3][4][5]. After a decade of effort including several field tests, it became clear that more intensive studies need to be conducted on uses and user requirements of such chairs in order to create a truly effective assistive tool. A mere series of technological innovations using the latest research results in electronics, intelligent robotics, and artificial intelligence (AI) is not sufficient. Public liability (PL) issues also have to be addressed before such chairs will become of common use in society. The author's own experience of becoming handicapped early in the decade (2001) tells that the issue of restoring mobility to the impaired or compromised is not so much technological but more psychological and philosophical in nature. The often unquestioned Cartesian view of the world, widely held by scientists and engineers as the only acceptable basis and methodology, is often in conflict with the daily reality faced by people with a serious handicap. Understanding the relationship between the chair, its user, and the environment supported by new developments in philosophy appears essential. Experience gained by building several intelligent wheelchairs is summarized and presented with key technical features of our chairs. This is followed by a design for a new intelligent wheelchair in which intelligent system technology is used more in an assistive role and not for achieving full autonomy.