The economic-mathematical model of the sustainability and predictability of the transportation system and the sea ports was considered as a single model encompassing those related to the financial sustainability and predictability of the enterprises. The author substantiated the expediency of creating the models by way of the logical probability simulation. 10 indexes were suggested for the evaluation of the financial standing of individual enterprises and the entire transportation system, with the method of golden section to be applied for the determination of the appropriate regulatory value thereof. The scenario-based tentative calculations were made and the results analyzed. The author proved that the logical probability simulation makes it possible to create an economic mechanism of striking a balance between the volume of traffic and the Budget payments with no administrative control