A vehicle drive assistance system is provided, which includes one or more processors configured to execute a general driver model learning engine configured to build a general driver model to be applied to a plurality of drivers based on driving data of the drivers, an individual driver model learning engine configured to build an individual driver model unique to a specific driver based on driving data of the driver, and an on-board controller provided in a vehicle operated by the driver. The individual driver model learning engine includes a vehicle control updating program configured to cause the on-board controller to update vehicle control processing based on the general and individual driver models. The vehicle control updating program acquires the driver models and, according to a given condition, determines a driver model based on which the vehicle control processing is updated, between the general and individual driver models.