A management assistance system can include: an imaging device; a first monitoring device; a second monitoring device; an instruction terminal; and a server. The instructing terminal can be configured to determine whether or not the caution determination condition is satisfied based on first monitoring information transmitted from the first monitoring device and second monitoring information transmitted from the second monitoring device, and transmit a dashcam video cut instruction signal to the imaging device when determining that the caution determination condition is satisfied. The imaging device can extract information of a predetermined time width including a reception time of the dashcam video cut instruction signal from the continuous dashcam video information to create dashcam footage information, associates the dashcam footage information with date and time information and identification information, and transmits the dashcam footage information to the server.