The purpose of cartographic generalization is to represent a particular situation adapted to the needs of its users, with adequate legibility of the real situation and its perceptional congruity with the representation. Interesting are those situations which to some degree vary from the real situation in nature. This is purposeful generalization where attention is directed towards particular, thematically valuable objects and their details. Difficulties in accomplishment of the cartographic generalization objectives are reflected in the basic approach. Some cartographers encourage the idea of complete prevalence of subjective approach to the process, yet accepting partial solutions that enable automated data processing of certain chart elements. Others stand for objectifying of all procedures, or schematic solving of all issues in the process, which will gradually lead up to the level where it could be termed automated. The latter is considered more acceptable by the authors of this paper, implying the necessary human intervention in the generalization, yet not to determine the course of the process, but just to act as a mediator.