This study attempts to formulate a conceptual and operational model that encapsulates the highlights of scientific sustainability research and that identifies the critical success factors of sustainable development from the perspective of different stakeholder groups. It seeks to identify viable consensus pathways in sustainable development strategies that are marked by conflicts among different stakeholders. To do so, this study focuses on three case studies that are part of the EU project SMILE, its way of sustainability thinking, and its stakeholders to encapsulate different sustainability approaches and different needs for sustainable development. To identify critical success/failure factors in the search for sustainable development at the interface of economic, environmental, and social factors, we use interview results, first, to compose case study-specific pentagon models. These models offer a systematic framework for sustainability and, in general, distinguish between five key forces, that is, software (e. g., knowledge), hardware (e. g., research facilities), finware (e. g., financial support), ecoware (e. g., environmental amenities), and orgware (e. g., institutional support systems). In a second step, we use both the questionnaire results and a multi-criteria spider approach to quantify the relative importance of the pentagon factors for each stakeholder group. This way we are able to develop stakeholder-specific pentagon models. Although there are many applications of the basic pentagon model in the sustainability literature, our attempt can be seen as the first one that combines cases at different time and spatial scales to generalize the interfaces between scientific research and policy arenas.