Maintenance is an essential part of long-term overall equipment effectiveness. Therefore, it is essential to evaluate maintenance policies’ effectiveness in addition to planning them. This study provides a classification of technical systems for selecting maintenance effectiveness indicators and a classification of maintenance models for calculating these indicators. We classified the systems according to signs, such as system maintainability, failure consequences, economic assessment of the failure consequences, and temporary mode of system use. The classification of systems makes it possible to identify 13 subgroups of systems with different indicators of maintenance effectiveness, such as achieved availability, inherent availability, and average maintenance costs per unit of time. When classifying maintenance models, we used signs such as the system structure in terms of reliability, type of inspection, degree of unit restoration, and external manifestations of failure. We identified one hundred and sixty-eight subgroups of maintenance models that differed in their values for specified signs. To illustrate the proposed classification of maintenance models, we derived mathematical equations to calculate all considered effectiveness indicators for one subgroup of models related to condition-based maintenance. Mathematical models have been developed for the case of arbitrary time-to-failure law and imperfect inspection. We show that the use of condition-based maintenance significantly increases availability and reduces the number of inspections by more than half compared with corrective maintenance.