An emerging strategy to combat homelessness is the development of “tiny homes”. However, the advent of tiny homes as a new form of housing intervention raises a number of questions about their intentions, efficacy, and policy feasibility. This paper seeks to understand the strategies used by stakeholders to plan, design, and implement a tiny home community to meet the needs of those experiencing homelessness, and to understand where these plans were effective and where challenges arose in meeting the intended project goals. Utilizing the recent development of Tallahassee’s “The Dwellings” project as a case study, we examine how the community was planned, resident experiences, and constraints to implementing a tiny home development. We use qualitative methods that include interviews with stakeholders who were integral to the planning and development process. Our findings highlight how funding constraints and NIMBYism (Not in My Backyard-ism) stymied stakeholder efforts to achieve equity and affordability at The Dwellings, resulting in the inability to achieve project aims of developing housing that serves the homeless population. We conclude by offering some observations and lessons learned for future research on tiny homes as a solution to ameliorate homelessness.