At the current pace of growth and innovation, electronic commerce sites will find it increasingly difficult to give customers the feeling of a personal and directed service that will ultimately make the difference. Content management and personalisation pose some of the most important challenges for online businesses, E-Society, Egovernance and E-government. The increasing need in the design of advanced interactive hypertext systems such as closed corpus (eg multimedia courseware) and open corpus (eg WWW) is for the user to access and manipulate large heterogeneous digitised resource bases efficiently, effectively and comfortably. Research in content management, usability mining, personalisation models and ontologies will crucially underpin the 21st century personal and business computing environment for knowledge discovery, access, manipulation, learning and management. To cope with the massive rates of information exchange in the new digital economy, the emergent IS environment will need to be able to rely on efficient contextually aware navigation, retrieval and transaction systems. These capabilities will have to be made available on both multicasted or on-demand media services, to serve a wide variety of social and business needs such as Electronic and Mobile Learning and Commerce as well as life-long e-foraging for leisure, cultural and general interests by anyone, anywhere through any terminal world-wide. We outline the central technical, social and ethical issues in capturing, managing and interpreting usability data intelligence on the roots of, and the routes to, user (dis)satisfaction. We describe the current technical shortcomings of browser, navigation and traffic management technology. We present our research focus in seeking to take a transformative step towards the development of a new IS persona for computer-aided navigation systems (eg CAIN, Lamas et al ’99) or Workflow-embedded document retrieval systems (eg SmartDoc, Badii ’97) as integrated with our online usability evaluation systems (PopEval_MB, WebEval_AB, Badii & Murphy ’99, Badii, ’99b, 2000 a,b,c).