Achieving sustainable development requires strategic efforts involving the entire organization. Maintenance efforts also play an important role. Company management needs to understand and develop an appropriate strategy to achieve sustainable development by applying maintenance performance measurements. The aim of this paper is to present possible ways of analyzing and ranking the impact of certain criteria with respect to achieving sustainability. The paper uses the method of Structural Equation Modeling—SEM in order to determine the most influential variable on the sustainability of maintenance of technical systems. Based on the set theoretical system model, for all its variables in the model, statements were made that describe them, on which 136 respondents gave their views (from 1 to 5, Likert scale) in the territory of the Republic of Serbia. An intuitive F-DEMATEL method was also used to prioritize variables. A team of 10 experts in the field of maintenance of technical systems was compared the criteria A—Application of technical diagnostics, B—Management of maintenance resources, C—Maintenance process planning, and the dependent variable D—Sustainability of maintenance of technical systems. According to experts, the importance of the criteria coincides with the results obtained by a survey with 136 respondents.