A system and method identifies vehicles to be included in a multi-vehicle system that is to travel along one or more routes for an upcoming trip, and determines plural different potential builds of the multi-vehicle system. The different potential builds represent different sequential orders of the vehicles in the multi-vehicle system. The system and method also simulate travels of the different potential builds for the upcoming trip, calculate a safety metric, consumption metric, and/or build metric for the different potential builds based on travels that are simulated, and generates a quantified evaluation of the safety metric, consumption metric, and/or build metric for the different potential builds for use in selecting a chosen potential build of the different potential builds. The chosen potential build is used to build the multi-vehicle system for the upcoming trip.