Gear condition monitoring is vital to safeguard the proper operation of high-end machinery, such as wind turbines. It plays a crucial role in ensuring the reliability and performance of these critical systems. The accurate monitoring of the gear degradation enables data-driven decisions, yielding to enhanced maintenance practices and substantial resources savings. In this comprehensive investigation, several monitoring techniques are being investigated, including surface topography, vision systems, oil quality monitoring, vibration monitoring, and safety sensors. These techniques are being integrated into an industrial-grade FZG gear test rig, enabling the testing of the components in real-life conditions. Endurance tests lasting 200 hours were performed focused on the controlled generation of gear pitting. The gear health was monitored with a dual approach: direct observations through cutting-edge vision systems and indirect assessment through vibration monitoring techniques. The evolution of the gear pitting was quantified using the images acquired with the vision system. The visual records showed an increase in pitting damage with the elapsed test duration. Besides, a similar trend was noted in the vibration level measured with accelerometers. In conclusion, the holistic approach enables detailed assessment of the gear damage, offering valuable insights and promoting better understanding of the evolution of the gear damage.