Academic urban debates shrouded with paradox render the transition to sustainable urban development (SUD) vague and unclear. The premise of this study is that the elimination of the controversial points included in each issue, in addition to reconciliation among these issues, may propel SUD. Therefore, this study dialectically discusses five urban issues: urban form, urban growth, transportation, urban vegetation, and governance (social participation). These issues were chosen among ten issues reviewed in a previous study in order to highlight controversial aspects and how to overcome them. The study suggests that the sociocultural dimension is an overlooked aspect in urban issues, and this may be a major reason for the conflict among academics. Further, this study concludes that governance is a major coordinator that can remedy the controversial points related to urban problems. Transportation is the second mediation among urban form, growth, and vegetation. Therefore, greater concern with governance and transportation in any urban planning policy improves current and future sustainable developments.