Place-based urban planning and design policies and practices—placemaking—often have winners and losers. Some people and communities may welcome new amenities and improved services as well as the increased economic and social profits derived from placemaking practices; on the other hand, certain social groups or geographic areas could be excluded from the benefits due to misconceived design or mismanagement of public resources and project activities, or rising prices in those places that accompany the new amenities. This dissertation mainly looks at the costs or unintended consequences of placemaking policies and practices in urban environments through three empirical studies, each of which explores different topics and dimensions by employing a variety of quantitative analytical tools and data science techniques. First, I examine the impacts of a place-based public financing policy, specifically Chicago’s Tax Increment Financing, on the survival and failure of existing and new business operations, using a survival analysis with multi-year business license datasets. Second, I use a latent profile analysis to identify the complexity and diversity of neighborhood typologies in which urban green spaces are either concentrated or sparsely distributed across geographically and socially diverse groups of society in New York City, associated with environmental justice and gentrification issues. Lastly, using natural language processing techniques combined with a Difference-in-Difference quasi-experimental approach, I investigate the relationships between urban public spaces—both publicly and privately owned public spaces—and human cognitive and behavioral patterns expressed on social media in Manhattan, New York City, in response to unforeseen environmental challenges, such as COVID-19 pandemic. Overall, the dissertation research advances understanding of the interrelationships between people, places, and planning practices from a diverse and multifaceted point of view. Findings from each chapter, along with the proposed methodological strategies, could provide valuable implications for planners and policymakers in the design, management, and decision-making processes in a way that balances the needs of geographically and socioeconomically diverse neighborhoods and urban places, not only to maximize the positive effects in placemaking cycles but also help mitigate potentially adverse consequences that may arise from those actions.