Sustainability policy evaluation and assessment seeks to answer the key question, sustainability of what and whom? Consequently, sustainability issues are multidimensional in nature and feature a high degree of conflict, uncertainty and complexity. Social multi-criteria evaluation (SMCE) has been explicitly designed for public policies; it builds on formal modelling techniques whose main achievement is the fact that the use of different evaluation criteria translates directly into plurality of values and dimensions underpinning a policy process. SMCE aims at being inter/multi-disciplinary (with respect to the technical team), participatory (with respect to the community) and transparent. SMCE can help deal with three different types of sustainability-related policy issues: 1) epistemological uncertainty (human representation of a given policy problem necessarily reflects perceptions, values and interests of those structuring the problem); 2) complexity (the existence of different levels and scales at which a hierarchical system can be analyzed implies the unavoidable existence of non-equivalent descriptions of it both in space and time); and 3) mathematical manipulation rules of relevant information (compensability versus non-compensability, preference modelling of intensities of preference, mixed information on criterion scores, weights as trade-offs versus weights as importance coefficients, choice of a proper ranking algorithm). This paper focuses on the these three issues and provides an overview of the SMCE approaches to them.