How do development processes impact sustainability on a citywide scale? This thesis initiates a significant conversation regarding city planning, design, and development processes through four development case studies: two in Houston, Texas, and two in Portland, Oregon. Houston and Portland maintain seemingly diametrically opposed land development processes, and as such define the outer boundaries of the spectrum. By studying the outliers, other urban areas should be able to place themselves on this spectrum, eventually deciding which lessons are applicable to their specific context. Further, I have explicitly chosen one controversial and one noncontroversial case study for each city to research an underlying hypothesis: does constructive conflict result in more sustainable development? Methods included studying development models and interviewing actors who participated in the development process in the case studies. Throughout the research, consistent themes emerged, even in seemingly opposite approaches to land development. First, there was overwhelming consensus among actors in the development process that developers hold considerable influence on the sustainability of the built environment, and are canonically the empowered decisionmakers in the process. Second, there is no ideal or one-size-fits-all development process for all cities, but there are consistent steps and contextual best practices which should be included. These steps largely revolve around broad-based community support and creation of accountability. Third and perhaps most importantly, the research suggests that constructive conflict does tend to create more sustainable development. Fourth and last, the benefit the development provides to the surrounding community should be prioritized. By analyzing planning, design, and development processes which are often muddied and unclear, I hope to have swept some dirt off of the path to a sustainable built environment.