Land-use decisions, particularly in an agricultural setting, lie at the nexus of the colliding challenges of climate change and food insecurity. Understanding and guiding these decisions at the regional scale is a key strategy in the development of natural climate solutions and sustainable food production systems. These issues come together in a particularly high-stakes context in the Massachusetts cranberry industry, which occupies a position of significant economic and sociocultural importance in the region, but faces a number of challenges in the form of heightened competition, unstable prices, an aging farmer population, and changing ecological conditions. Many farmers are looking either for ways to become profitable, or to exit the industry in a financially sustainable way. One option is to sell their land to developers; another option, which is exciting to scientists and environmental advocates, is undergoing an active habitat rehabilitation to restore the beneficial ecosystem services of a functioning wetland environment. Integrating satellite data and in-situ sensor data collected over the past decade, we aim to conduct a systems analysis that unites the viewpoints of cranberry industry stakeholders and clarifies the trade-offs between environmental, economic, and social factors in the region. We propose to address this aim via three core research efforts: a contextual analysis of the industry; a valuation and mapping of key ecological, economic, and social factors; and an integrated modeling approach that models interactions and trade-offs between these factors. In particular, this presentation will focus on the progress we have made valuing and mapping key environmental and economic factors using publicly available satellite imagery and census data. This work demonstrates how these factors align with existing features of the natural and built environment, supports conservation organizations and municipalities in their restoration and conservation advocacy, and provides a foundation for future scenario mapping that will analyze trade-offs in different land use cases.