Ecologically conscious watershed management is not a new concept. It presents numerous benefits but also incurs economic costs. This study posits that NYC presents an exemplary case for which other metropolitan areas can adopt in establishing a symbiotic relationship with its hinterlands. Both creating efficient allocation of scare resources and reducing overall anthropogenic impact on the biota. In comparing the effectiveness of capital investments in Green and Grey water infrastructure in seven upstate New York (NY) watersheds from 1962-1998, this paper uses a quasi-experimental regional approach to explore the benefits and trade-offs of water infrastructure capital investments and policy decisions. Thereby allowing for a more mutually beneficial and sustainable urban-rural relationship to develop.