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Although indicators in rating systems have been initiated to measure and promote the sustainability performance of roadway projects in some developed countries, applying those indicators to other regions/countries may still be difficult. In response to the United Nations’ sustainable development goals, local road agencies in Taiwan urgently need to establish systematic and quantifiable sustainable roadway strategies. As part of the project to develop a green urban road rating system in Taiwan, this study aims to develop transportation livability-related indicators (TLIs) and identify critical barriers to TLI application in Taiwan’s urban road system. To this end, the research employed an adaptive approach that integrates top-down and bottom-up approaches. The top-down approach included the comprehensive literature review and panel discussion to derive four TLIs and 21 corresponding requirements, and nine potential barriers to hold the indicator adoption. Four TLIs are pedestrian facilities, universal design, multimodal transportation, and utility facilities. The bottom-up approach used the Analytic Hierarchy Process (AHP) to assign weights to proposed indicators/requirements. Four critical barriers were also investigated through the Weighted Sum Model (WSM) method, namely unfavorable in-situ conditions, lack of stakeholders’ coordination, unsupported government policy and regulation, and limited budget and schedule. The findings can be beneficial to engineers and decisionmakers to enhance the livability standard of urban streets. The framework proposed in this research can be applied to other roadway characteristics aspects in different regions/countries.