This article presents the development and implementation of an analytical system for the comprehensive assessment of the viability of urban and rural settlements. The proposed assessment approach was experimentally tested using settlements in the Volgograd region as a case study. The system utilizes data from open sources, including OpenStreetMap, municipal statistics, and the results of geoinformation analysis, to generate indicators based on key criteria reflecting infrastructural, environmental, social, and economic development of the territories. Each settlement is evaluated based on a variety of parameters: from the accessibility of medical and educational infrastructure to the level of greening, facility load, and land use priorities. The study employs algorithmic data processing using Python and specialized libraries (OSMnx, pandas, geopandas), and the results are visualized through an interactive map (Leaflet) and tables. A key feature of the project is the integration of diverse indicators into a single assessment score, displayed on the regional map and in tabular form. The results can be used by local authorities and research organizations to make informed decisions in the field of spatial planning and quality-of-life improvement. The developed system demonstrates flexibility, scalability, and applicability to other regions given the availability of relevant source data.