Transport is an important element of a local, interregional, and global economy. For this reason, the condition and development of transport systems, their links, entire chains, and sectors, are systematically assessed. This article reviews the literature (by the PRISMA method on WoS database), using the keywords: “assessment”, “development”, and “transport systems”, to identify the most frequently used methods and assessed factors. Initially found 108211 records, narrowed down to 90 (including open access, English language, published 2019—May 20, 2024). Based on the research, several quantitative and qualitative methods were indicated (with the dominant role of MCDM methods, suggested as a tool for building a model allowing the comparison of transport systems) and the main groups of assessed factors (transport factors, economic factors, safety factors, social factors, political and business environment factors, and natural environmental factors, suggested as factors to be assessed in a model). The research results presented constitute the basis for building a model that enables the comparison of the transport systems of individual branches under various geopolitical conditions.