New York City is a place where one in three children live in poverty, and where more than 50,000 citizens sleep in homeless shelters. Increasingly, middle- and low-income citizens find it close to impossible to secure a home, often thwarted by spiraling debt and the encroachment of real-estate speculation. Van Alen Institute, in partnership with Miguel Robles-Duran and Gabriela Rendón, founders of Cohabitation Strategies and professors at the School of Design Strategies at Parsons The New School for Design, hosted a workshop to bring together researchers, designers, and activists on the forefront of strategizing ways to reverse these cycles of debt and displacement. Facilitators included Rob Robinson, housing rights advocate, co-founder of Take Back the Land, and active member of the National Economic and Social Rights Initiative; and Lorenzo Romito, architect, artist and co-founder of Stalker and Osservatorio Nomad. Through games, short presentations, and discussions, we built an understanding of the processes at work, in order to analyze the role that government, nonprofit organizations, designers, and cultural organizations can play in addressing this crisis of affordability.