According to the current European conditions, culture-led urban regeneration policies and practices are being enhanced by the introduction of interdisciplinary innovative approaches. These involve the development of methodologies and tools that are able to address material and immaterial networks of microcommunities in a systemic and circular manner of thinking among cultures, economies, and processes. When talking about overturning hierarchies and power relations and creating the conditions that are necessary to encourage a new collaborative cultural regeneration of urban public spaces and places, some open questions can be relevant: What kind of cultural resources do we have to optimize for achieving local sustainable development in response to global challenges? What kinds of new uses for public spaces and places must we improve in order to generate complex values and enhance the engagement of communities? How could communities activate themselves for building complex values networks? In order to understand how positive initiatives are activated as a "chain reaction" and facing unsolved conflicts and building new productive values systems tailor-made for a specific context are made possible, the present paper explores the components of new forms of local complex values networks in regeneration processes, based upon the ex-post evaluation of some selected Italian practices with the multi-criteria method PROMETHEE-GAIA.