This study is useful for railway operators as it enables them to verify their decisions against the results of the application of the techniques of strategic planning and multi-criteria analysis. It gives railway stakeholders concise, objective and unbiased information so that they can then make decisions and also allows them to determine the strengths and sensitivity, of the best solution found. This paper presents a methodology for the assessment of the policies of railway operators using Strengths–Weakness–Opportunities–Threats (SWOT) criteria and the Sequential Interactive Modelling for Urban Systems (SIMUS) method. The methodology of the research consists of two stages. In the first stage, the alternatives of the policies for the railway operator are formulated; the criteria in the SWOT group are defined; and the values of the criteria are determined for each of the alternatives. In the second stage, the SIMUS method is applied to rank the alternatives and assess the criteria in the SWOT groups. The criteria are interpreted as objectives and linear optimizations are performed. A comparison between the desired values for each objective of the SWOT criteria and the optimum values of the objective functions obtained by SIMUS was made. The methodology was applied to the Bulgarian railway network. Three policies for railway operation were studied. The total number of 17 railway policies criteria in the SWOT group were defined and assessed—three strengths criteria, seven weaknesses criteria, three opportunities criteria and four threats criteria. The results indicated that the best strategy is A3 (some reconstruction of the railway infrastructure and new rolling stock on some lines), with the highest score of 3.76, followed by A2 (new rolling stock on some lines), with a score of 2.71. The status-quo strategy (A1) has a very low score of 0.43, that the current situation or status-quo cannot be supported. The weights of both strengths and opportunities are both of the same importance with a weight of 0.180. It was found out that the clusters Weakness and Threats are dominant with weights of 0.4 and 0.24 respectively. The results show that the weights are all practically the same, about 0.06, and therefore, no discrimination by importance is possible. The methodology makes it possible to consider the alternatives simultaneously, and in this way, the results will reflect the effect of one criterion on all others, and permit us to quantify the differences between expected and real results.