The spatial and temporal transformation of a territory and its settlement system is a classic subject of study in socio-economic geography. The aim of our research was to develop tools for applying non-statistical methods when analyzing these processes. This article discusses the possibility of using non-statistical methods for evaluating processes that describe the population and the regional development. The authors have analyzed databases collected through the Vkontakte social network and the Yandex search engine. The spatial heterogeneity in the development of the Pskov region’s territory, reflected in the Internet activity of the population, is demonstrated; six types of municipal districts have been identified according to the attractiveness and intensity of their development. There has been revealed heterogeneity in the gravitation of external actors of the territory’s transformation (primarily those from St. Petersburg). The obtained data are compared with data presented in some statistical sources.