A method performs an automated measurement of dimension(s) of an arriving vehicle arriving at a parking area. The method obtains a skills assessment of a driver of the arriving vehicle, which indicates skill level of the driver in performing parking maneuver(s). The method dynamically defines, based on the dimension(s) of the arriving vehicle and the obtained skills assessment, a parking space in an unoccupied area within the parking area. The defining includes selecting dimensions of the dynamically defined parking space. The method directs the arriving vehicle to the dynamically defined parking space, the directing including providing live parking guidance to facilitate maneuvering the arriving vehicle into position in the dynamically defined parking space.