There is provided a system and the like capable of assisting remote operation of a work machine performed by a remote operator in such a way that contact between the work machine and an actual machine operator and other unfavorable situations can be avoided. Even in a situation in which a first evaluation result is affirmative and a work machine 40 can be remotely operated via a remote operation apparatus 20, but in a situation in which a second evaluation result is affirmative and it is highly probable that a worker carrying a portable terminal 60, such as an actual machine operator OP2, is so close to the work machine 40 or on the work machine 40 that short-range wireless communication between the work machine 40 and the portable terminal 60 is established, remote operation of the work machine 40 is inhibited.