The onset of COVID-19 in New York has created impossible financial situations for tenants, and resultingly, for landlords, many of whom are themselves family owned businesses with tight financial concerns and obligations of their own. Despite a landlord or tenant’s best efforts, it is inevitable that a landlord may need to remove a tenant from their rental property. In this article, we evaluate the pros and cons of different approach in the residential context of New York both under normal conditions and considering the special circumstances presented by COVID-19, including the increasing benefits of turning to “Cash for Keys.”