Transportation planning and urban development in the United States have synchronously emerged over the past few decades to encompass goals associated with sustainability, improved connectivity, complete streets and mitigation of environmental impacts. These goals have evolved in tandem with some of the relatively more traditional objectives of supply-side improvements such as infrastructure and capacity expansion. Apart from the numerous federal regulations in the US transportation sector that reassert sustainability motivations, metropolitan planning organizations and civic societies face similar concerns in their decision-making and policy implementation. However, overall transportation planning to incorporate these wide-ranging objectives requires characterization of large-scale transportation systems and traffic flow through them, which is dynamic in nature, computationally intense and a non-trivial problem. Thus, these contemporary questions lie at the interface of transportation planning, urban development and sustainability planning. They have the potential of being effectively addressed through state-of-the-art transportation modeling tools, which is the main motivation and philosophy of this thesis. From the research standpoint, some of these issues have been addressed in the past typically from the urban design, built-environment, public health and vehicle technology and mostly qualitative perspectives, but not as much from the traffic engineering and transportation systems perspective---a gap in literature which the thesis aims to fill. Specifically, it makes use of simulation-based dynamic traffic assignment (DTA) to develop modeling paradigms and integrated frameworks to seamlessly incorporate these in the transportation planning process. In addition to just incorporating them in the planning process, DTA-based paradigms are able to accommodate numerous spatial and temporal dynamics associated with system traffic, which more traditional static models are not able to. Besides, these features are critical in the context of the planning questions of this study. Specifically, systemic impacts of suburban and urban street pattern developments typically found in US cities in past decades of the 20th century have been investigated. While street connectivity and design evolution is mostly regulated through local codes and subdivision ordinances, its impacts on traffic and system congestion requires modeling and quantitative evidence which are explored in this thesis. On the environmental impact mitigation side, regional emission inventories from the traffic sector have also been quantified. Novel modeling approaches for the street connectivity-accessibility problem are proposed. An integrated framework using the Environmental Protection Agency's regulatory MOVES model has been developed, combining it with mesoscopic-level DTA simulation. Model demonstrations and applications on real and large-sized study areas reveal that different levels of connectivity and accessibility have substantial impacts on system-wide traffic---as connectivity levels reduce, traffic and congestion metrics show a gradually increasing trend. As regards emissions, incorporation of dynamic features leads to more realistic emissions inventory generation compared to default databases and modules, owing to consideration of the added dynamic features of system traffic and region-specific conditions. Inter-dependencies among these sustainability planning questions through the common linkage of traffic dynamics are also highlighted. In summary, the modeling frameworks, analyses and findings in the thesis contribute to some ongoing debates in planning studies and practice regarding ideal urban designs, provisions of sustainability and complete streets. Furthermore, the integrated emissions modeling framework, in addition to sustainability-related contributions, provides important tools to aid MPOs and state agencies in preparation of state implementation plans for demonstrating conformity to national ambient air-quality standards in their regions and counties. This is a critical condition for them to receive federal transportation funding.