Working towards an equality of differences of a city’s diverse cultures and subcultures requires an examination of the realities of how municipal and provincial legal frameworks governing the city space—such as urban planning policies, zoning decisions, and bylaw enforcement—play out within the microcosm of the everyday neighborhood, where conflicting life patterns must coexist even when they are at odds. Drawing on an urban legal anthropology and urban legal geography methodology assessing the realities of the life of subcultural communities in the city space, this paper’s objective is to explore potential paths towards an equitable regard and valuation of the different ways of knowing and being in the context of city redevelopment and cultural sustainability.