An adaptable vehicle monitoring system is disclosed. The system includes a core platform having a state monitoring subsystem and a feedback subsystem. The core platform interconnects a perception subsystem, a knowledge acquisition subsystem, and a user interface. The perception subsystem is configured to acquire current vehicle state data from instruments of a vehicle. The knowledge acquisition subsystem includes a context awareness subsystem configured to determine a current vehicle context. The state monitoring subsystem is configured to derive a current vehicle state based at least in part on the vehicle state data and vehicle context. The knowledge acquisition subsystem further includes a database subsystem configured to store the current vehicle state data, current vehicle context, and current vehicle state. The trend monitoring subsystem is configured to analyze the one or more stored vehicle state data, stored vehicle contexts, and stored vehicle states to identify one or more trends. The feedback subsystem is configured to prepare operator and deliver operator feedback via the user interface based at least in part on a comparison between the current vehicle state and/or current trend and an expected vehicle state and/or previously identified trends.