The senior housing shortage is an urgent problem not only in New York City but also across the United States. In New York City, there are nearly 200,000 seniors on the waiting list for a senior housing incentive and have been waiting an average of seven years (Hosey, 2021). This paper critically examines New York City’s various policies, organizations, programs, and initiatives that aim to alleviate the housing shortage for seniors in order to 1) understand New York City’s efforts, 2) to assess the failures and successes of those efforts, and 3) to propose new possible ways forward in the next decade. Using the SWOG analysis method (Strength, Weakness, Opportunity, Gap), the paper analyzes and studies a variety of ongoing initiatives and identifies several recurring challenges and issues: the scarcity of land resources, the complexity and burdensomeness of government processes, the efficiency of the government departments and organizations, income and rent issues for seniors, and issues of controversy and balancing. This paper then concludes with recommendations and strategies that attempt to alleviate the senior housing crisis in New York City using six key “strategy shifts” as a reference point.