Context-sensitive solutions, value engineering or value analysis, and asset management systems are all strategic processes or systems with common objectives, even if they have different emphases. All place a high value on customer satisfaction, stakeholder values, and the delivery or maintenance of safe facilities. All stress the efficient and effective use of resources and the alignment of investments to produce the best outcomes or the most quality for the money. All are open to a broad interpretation of the word “best,” but they are challenged by the measurement of performance in areas that are more difficult to quantify. They share an emphasis on transparency, multidisciplinary teams and perspectives, and analytical, evidence-based decision making. They use processes that examine multiple alternatives to finding consensus on ultimate decisions. Especially when they are used together or in tandem, these tools and systems can be used as part of strategic and systematic approaches that have a significant potential for the delivery of transportation assets with greater sustainability and public funding and support for transportation, the community, and the natural environment. This paper examines the principles, similarities, and opportunities for reinforcement of these approaches.