“The Location Optimization Plan Plus,” published in 2024, suggests that many cities in Japan should aim for a compact-plus-network approach based on “Urban conditions” and “Urban challenges” under depopulating society. In this study, “Urban conditions” are defined as the urban structural characteristics (land use, buildings, infrastructure, and population). Then, we categorized 1740 cities in Japan based on these urban structural characteristics. As a result of cluster analysis, they were classified into 30 categories. Through the result, it was clarified that the characteristics and issues difference among categories. In addition, we summarized key issues for planning future urban restructuring.