Information Society is advancing along a route of ecosystemic evolution. ICT and Internet advancements, together with the progression of the systemic approach for enhancement and application of Smart Systems, are grounding such an evolution. The needed approach is therefore expected to evolve by increasingly fitting into the basic requirements of a significant general enhancement of human and social well-being, within all spheres of life (public, private, professional). This implies enhancing and exploiting the net-living virtual space, to make it a virtuous beneficial integration of the real-life space. Meanwhile, contextual evolution of smart cities is aiming at strongly empowering that ecosystemic approach by enhancing and diffusing net-living benefits over our own lived territory, while also incisively targeting a new stable socio-economic local development, according to social, ecological, and economic sustainability requirements. This territorial focus matches with a new glocal vision, which enables a more effective diffusion of benefits in terms of well-being, thus moderating the current global vision primarily fed by a global-scale market development view. Basic technological advancements have thus to be pursued at the system-level. They include system architecting for virtualization of functions, data integration and sharing, flexible basic service composition, and end-service personalization viability, for the operation and interoperation of smart systems, supporting effective net-living advancements in all application fields. Increasing and basically mandatory importance must also be increasingly reserved for human-technical and social-technical factors, as well as to the associated need of empowering the cross-disciplinary approach for related research and innovation. The prospected eco-systemic impact also implies a social pro-active participation, as well as coping with possible negative effects of net-living in terms of social exclusion and isolation, which require incisive actions for a conformal socio-cultural development. In this concern, speed, continuity, and expected long-term duration of innovation processes, pushed by basic technological advancements, make ecosystemic requirements stricter. This evolution requires also a new approach, targeting development of the needed basic and vocational education for net-living, which is to be considered as an engine for the development of the related 'new living know-how', as well as of the conformal 'new making know-how'.