Connectivity and the huge data availability today open doors for modern and adaptable maintenance solutions. Nowadays, clients have the desire, not only to avoid breakdowns, but also to find out how to use their systems in order to reduce the overall exploitation cost and expand the remaining useful life. Researchers of different areas have worked to achieve such goal, but a complete solution that quantitatively assesses for different actions, costs and the degradation evolution was not proposed. In this paper, we will consider the example of a fleet of vehicles. We will model different operational costs as well as the degradation trajectory of a real component, and account for two possible actions: mission planning and maintenance operations scheduling. We highlight how those two actions are connected and propose a method for finding the optimal usage of the fleet. Finally, through simulations, we compare it to a maintenance/exploitation policy that mimics real fleet usage.