This article presents a methodology that provides a continuous assessment of predictive maintenance (PdM) technologies with respect to specific business scenarios. The methodology integrates existing reliability and maintenance business analysis techniques and standards. The positive impacts that may have implementing these technologies have always been in mind. A critical simulation step is also added where different predictive maintenance strategies are simulated in order to obtain the optimal maintenance strategy. This Monte Carlo simulation relies on the reliability information based on the probability density distribution of failure for the system or component, providing as a result the optimal strategy among the proposed options. The article finally explains how this methodology has a positive impact not only on the cost-effectiveness of maintenance processes, but also on the maintenance information available.