Accelerometer data has been gathered from accelerated conditioning in grease lubricated and lubrication deprived gear meshes in AH-64 helicopter intermediate and tail rotor gearbox, which are commonly problematic components of the Apache helicopter platform. These tests were performed in a controlled drive-train research test bed, simulating drive-train conditions to improve diagnostic and prognostic capabilities of Condition Based Maintenance (CBM) practices in Integrated Vehicle Health Monitoring System - Health Usage Monitoring System (IVHMS-HUMS) and other comparable CBM packages, as monitored by a standardized Digital Source Collector (DSC) system. Time-frequency representations of vibration measurement collected from two spaced sensors are used to provide signature analysis of transient system harmonics. Furthermore, the time-frequency mutual information advanced signal processing technique is then proposed and validated using vibration data. The measure advances the development of mutual information health indicators to quantify degradation of the helicopter power train. The AH-64 test systems perform under stress in realistic loading conditions and lifetime accelerated aircraft aging is monitored using the proposed advanced signal processing techniques for baseline tests for comparison with faulted conditions.