Design solutions addressing climate resilience and sustainable development are desired for policy application, yet often encounter friction within the design team as well as between designers and external community members. Factors include unfamiliarity with issues and strategies, resistance to innovation, and constraints of time and budget, among others. Here, we aimed to understand how design may be supported through adapting the established practice of Value Methodology to better address policy goals. Action research methods adapted the standard Value Methodology process by collecting community inputs and addressing second law considerations. Challenges related to stakeholder concerns, practitioner preferences, and uncertainty under future conditions, especially climate change, were addressed by applying Multi-Criteria Decision Analysis to elicit community value expressions. Absent detailed forecast or scenario analysis, entropy-based qualitative assessment was applied in proxy for resilient approaches. The adapted Value Methodology approach was applied for collaborative innovative design across green buildings, net-zero military installations, regional climate resilient infrastructure systems, and multi-state renewable energy developments. Examination of how and when parties shared inputs indicated general patterns revealing user acceptance. Through cumulative action research across multiple cases, our study revealed that entropy assessment aided systems-level problem-solving during community and designer workshops to guide problem definition, generate designs, and evaluate alternatives. Additionally, outcomes were improved when stakeholder input was obtained early and repeated iteratively. The main findings are drawn from practitioner and stakeholder responses which may provide input to shape further research and practical use in the field as design teams seek practical ways forward for complex assignments.