The debate on the sustainable perspective of a circular economy and MSW (Municipal Solid Waste) management is no longer focused on the resolution of an emergency and on the pure technicality of creating efficient services. New light has been shed on the operational phase, as often unresolvable technical-environmental issues during service management lead to a state of decay, affecting urban vulnerability and users’ involvement. The research aims to develop an auxiliary tool for public administrations in planning a zero-waste future whilst enhancing the urban landscape. This study considers the perspective of virtuous management of the resource flow cycle along with evaluating implementable theoretic models, operational scenarios, and technological tools that can be integrated into a specific built environment. The first phase consisted in the definition of the involved subjects and the evaluation criteria for the impact of the service management system. The second phase includes the definition of operational strategies for virtuous and sustainable management of resource flows, intended as opportunities for the regeneration and development of the local context. The result of this research work is the elaboration and experimentation of an information system for the evaluation of the integrability of operational scenarios with the systemic, quantitative, and qualitative elements that characterize an urban landscape. The selected actions and technologies have been assessed in terms of short-term feasibility, cost-effectiveness, and local efficacy. This research work shows that many urban contexts with efficient services have been conceived as ecosystems, integrated into the landscape, driven by the synergy of institutions and operators, capable of carrying out the entire cycle from waste production to the marketing of recycled products. Our analysis shows that this issue can be effectively tackled through varied and mixed solutions; by integrating strategies, techniques, and scenarios, and by stimulating citizens’ involvement.