A transportation management system that includes tools for generating an optimized trip plan that can be updated, such as based on driver input, during implementation of a planned trip. The system includes a comprehensive trip optimization tool that generates a trip plan with fuel stop and rest stop optimization. The system includes tools calculating estimated time of arrival (ETA) and projected time of availability (PTA) for the driver, and these tools are adapted to provide the ETA and PTA for the entire trip (rather than only providing an ETA for the next stop). The system further includes tools accepting driver input and/or allowing driver manipulation of a dispatched trip plan such as using pre-filtered alternatives for fuel stops or rest stops or routes, e.g., based on stored driver preferences, that may be less optimal than those in the original trip plan but still viable.