The paper deals with the implementation of similarity-based approach decisions which are considered in detail (specific areas and cases in real life). The role of similarity, descriptive similarity, and numerical evaluation is comprehensively examined. The author pointed out that descriptive similarity is the relevant approach for equation of the statements. The paper introduces the transport situation similarity results in town of Ostroh (Ukraine) and certain Estonian towns, which is of great use for Ostroh public transportation claims. The author indicated that it is important to transform textual information into formulas. Artificial intelligence application needs of two level are under appreciate importance. To justify these decisions suitable algebraic formulas of system theory as well as experts’ logical steps are used.