The aim of this paper is to form an analytical and critical framework to consider the uses of digital platforms in heritage field and practices and to provide methodologies for user profiling based on the identification of local stakeholders and their needs. Within the context of the EU H2020 research project RURITAGE, a resource ecosystem (RRE) of various integrated tools was created for shaping and addressing heritage-led knowledge and bottom-up strategies of local regeneration. More specifically, the RRE was conceived to provide local stakeholders with new methodologies and user-friendly tools based on bottom-up processes for identifying and actioning heritage and territorial features and turning these cultural natural values—as well as the gaps—into opportunities. This paper undertakes a comparative analysis of the integration of tools in other digital platforms for heritage practices and/or regeneration processes to explore the holistic approach to heritage knowledge and the effectiveness in engaging local stakeholders. In addition, it frames methodologies for local stakeholder and related needs identification. Through this comparative analysis among digital heritage platforms and through user profiling to target the needs of users by using the RRE as a case study, the paper explores the challenge of helping communities to shape a local heritage-led collaborative knowledge supported by integrated and user-friendly digital tools and to activate them in preserving and exploiting their territories and building shared and plural cultural heritage understandings, considering cultural heritage as a social need.