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Evaluation of development programs, plans, projects is episodic task of local government in two basic complementary forms: ex ante and ex post, whose quality depends on establishment of a continuous monitoring process of territorial changes. Monitoring should enable the information and signaling provision to support both evaluation forms and addressing the problem issues during the implementation process. Experience shows that monitoring functionality means tracking different domains of territorial transformation and several sets of quantitative and qualitative indicators related to planned development targets. However, these reports, because of its sectoral specificities or indirect connection with development goals, are often incomprehensible to the general public. Therefore, some researchers focus is directed towards the development of a new Geographic Information Systems (GIS) functionality: monitoring of communities / cities vital signals that are far more related to existential values of the local community, and therefore more understandable and more acceptable to the general public. This paper provides a critical review of conceptual thinking on the functionalities of GIS based monitoring and review of good practice in the development of technical solutions in this field. The results of this study indicate the need for changes in the approach to designing a web-based GIS applications for monitoring and evaluation. [ABSTRACT FROM AUTHOR]