Homelessness continues to be a persistent and highly visible public health issue in New York City. New York/New York III, the current initiative that aims to expand supportive housing services for New York City’s chronically homeless mentally ill population, will expire in June 2016. In the context of shifting policies reflecting the growing popularity of the Housing First model, the authors of this paper call attention to the unique needs of the severely and persistently mentally ill (SPMI) homeless population. The authors propose that the current and future states of homelessness initiatives are inadequate in their levels of funding, coordination, and regulation, thereby negatively affecting New York City’s most vulnerable residents. Drawing on evidence from the literature, we compare the Housing First and traditional housing readiness models in New York City, the latter of which has become increasingly controversial in recent years. The authors provide suggestions for bridging the current gaps in research, policy, and practice in hopes of increasing accessibility and prioritizing housing for this population.