The research based on the analysis of existing theory of port development prediction and control reveals the contrariety between existing models and the requirements of practice. Historically formed toolkit briefed in previous publications of the authors and summarised in this article does not answer to the strategic question of the decision-makers about the development program of a given port. Existing models explain in detail why the port was developed in a particular way without elaborations of the exact directions for future development. Due to the nature of the studied subject it is impossible to create a single model of the process of port development using the traditional methodological principles, which fact is postulated in the article. Since the modern port is a complex, stepwise, multi-level dynamic system, it cannot be adequately mapped using traditional linear system, which is a methodological simplification of reality. As a result, the port models constructed within the linear paradigm suffer significant loss of properties, which from the outset limits the scope of their applicability. To study the strategic characteristics of port development, especially included in the associated spatial-economic clusters, it is convenient to make use of well-established research in other fields of knowledge. The principal task of the authors was not the transfer of the general provisions of this theory and the creation of a methodological concept which is already used in the transport business, but elaborating specific models of development, focusing on the study of the qualitative and quantitative characteristics of the studied objects. The paper represents the results of modeling the interaction and evolution of port populations serving the hinterland. The results confirmed the theoretical assumptions and the possibility of achieving stated goals.