This chapter dissects the complex network of rural-to-urban resource thresholds as a method to more clearly frame and comprehend the contemporary city. Through the process of isolation followed by collective inquiry, the “lines of engagement” can be understood as dynamic instances of engagement that collectively define not only the economic and political construction of the contemporary city, but also the urbanite’s collective memory and fragmented urban understanding. Through a process of value-based inquiry relative to food, money, and real estate, the chapter proposes a proactive intellectual framework for architects, designers, and urbanists to explore and comprehend the evolving contemporary urban condition. This value-based lens can support the identification of value-add opportunities in practice and the pursuit of a more socially equitable built environment.