We present a large-scale systemic intervention conducted in the wine village communities of Cyprus. The scientific aim of this paper is to contribute to expanding community operational research's purpose, scope, and tools by reflecting on a cascading engagement model of stakeholders toward regional development in Cyprus. An ad-hoc committee comprising three representatives of the Department of Town Planning and Housing, three members of the Cyprus Academy of Public Administration, and a few external consultants came up initially with about a dozen stakeholders’ categories they considered “relevant.” Using a stepwise (cascading) expansion, they eventually engaged over 200 actors representing 26 stakeholder categories. The first 29 stakeholders identified 71 obstacles to developing the wine villages using Structured Democratic Dialogue (SDD). They clustered the obstacles into themes and formed working groups to address them. Each group identified and invited experts and additional stakeholders they considered relevant to form extended theme-specific groups. Each group conducted a SWOT analysis to deepen understanding and produced a thematic vision map using SDD. A holistic vision map was constructed through a final SDD process in which participants were the authors of the most influential factors from each thematic vision map. The approach adheres to the bottom-up, community-led method and falls within community operational research and citizen science. The cascading model offers a formula for multi-methodological intervention. The stepwise bottom-up identification and engagement of stakeholders empowers and engages authentically, especially those marginalised. The expansion in numbers and the effective engagement of stakeholders creates the required momentum for societal change. We discuss the model's broader applicability, frame it within third-phase science, and suggest future directions.