The article provides a theoretical review of the literature on assessing the relevance of various aspects of community improvement. The authors have developed a toolkit for analyzing the population’s demand and level of satisfaction, including 15 indicators. Empirical data on the requests for the improvement of settlements have been collected on the territory of the South of Russia by electronic questionnaires 819 people, permanent residents of 18 settlements by random stratified sampling. Statistical analysis using the method of allocation of principal components in the program SPSS Statistics (version 21) allowed to develop models of the population’s demands on improving settlements of the Stavropol Territory. The applied modelling algorithm allows improving the decision-making system in the field of improvement of territories with the involvement of stakeholders’ opinions. Shows the possibilities of developing a transdisciplinary approach for quality improvement of people’s lives and sustainable development of territories.