Sevastopol is a region of the Russian Federation and at the same time a municipality with its own social and economic development trends. This is a city with rich military history and potential for tourism development, high level of education and culture, unique geographic location and climate. From the investment point of view, the region is attractive as it has a developed transport infrastructure, a warm-water seaport, developing wine production, ship building and maintenance, fisheries and fish processing, information technologies; green, history and wine tourism. At the same time, experts believe that Sevastopol has an insignificant investment potential and moderate investment risks. The article proposes a hypothesis on the interconnection of such performance indicators of the social and economic development as gross regional product, investment into the capital stock and annual average wages. It does not seem possible to analyse more indicators due to the statistic timeline limitations associated with the development of a model (objective data on Sevastopol is available only for 4 years). The interconnection of the variables has the multicollinearity effect that can produce false results. In order to make objective evaluations, the article presents the methodology for developing vector auto-regression equations and assess its parameters, a system of structural and reduced simultaneous autoregressive equations was presented, the unknown parameters were assessed. The simulation allowed to prove that the wages is not influenced by investments, or GRP, or vice versa. GRP grew due to investments that had been increased thanks to state support. The developed models and accumulated data can be useful for the authorities in terms of pro-active management. Further research will be aimed at assessing the feasibility of the performance indicators under the Strategy for the social and economic development of Sevastopol until 2030 taking into the account the results published in this paper.