Climate-change-induced hazards are causing large scale displacements of communities, destruction of property, and disruption of critical infrastructure. These increasingly unpredictable climate events result in complex and cascading impacts, emphasizing the need for comprehensive, data-driven, multidisciplinary design and planning toolkits. To effectively adapt to such unpredictability, these toolkits must consider a complex network of interdependencies – a range of interconnected factors, datasets, and stakeholders – that influence the planning process. With the emergence of powerful and accessible web-based computational capabilities, there is an opportunity to enhance risk management tools and allow for data-driven planning and design scenarios to support adaptive infrastructure provisions and retrofits. This paper shares the development of Flux.Land, an accessible and collaborative spatial decision support system (SDSS), allows community and planning agencies to visualize climate impacts and take collective action. In the context of flood-prone Broward County, Florida, this paper showcases how a large corpus of data-driven design and planning scenarios can be generated through the systematic definition of quantifiable design goals, evaluation metrics, and curation of computationally derived design recommendations. Through Flux.Land, we illustrate how data-driven, collaborative, web-based toolkits can be harnessed for data-driven planning and decision making across geographical, social, and environmental scales.