Performing site selection and coverage analysis in a dynamic market poses many challenges for analysts and developers. Whether using single or multiple criteria, scalability often becomes a problem. We will present a use case common in the healthcare industry to demonstrate how we apply spatial logic and heuristics to reduce processing load, utilize machine learning techniques to incorporate conditional criteria, leverage GeoAnalytics Engine and other big data tools to process the analysis at scale, and integrate ArcGIS Knowledge to review, explore, and monitor outcomes.