Yes, the issue is all about what is meant by a rope or chain being "taut". To me, it just means it is supporting tension at the place it attaches to the girl, so if there were slack present, it would straighten as the tension force arrives at the end and the rope goes taut. A signal arrives along the rope when the tension arrives. We can see that happening in the falling chain in the video-- at first there is no difference in the motion because the tension in the chain at the mass is zero, which we could notice by putting a slack wiggle into the chain as we dropped it, and waited for when that wiggle straightened (when the chain went "taut"). We should be able to see the tautness signal propagate along the rope, and arrive, as tension, at the mass. The tension originally in the chain, before the mass is released, should quickly go to zero as the two masses fall together, then later the one mass gets a jerk as the signal arrives and tension reappears at the end of the chain. But I can see that "never goes taut" could also mean that the chain is never hanging down completely straight, and the OP could be interpreted like that, in which case the rope could support tension prior to being "taut", like in the video. It may be the intention of the question that the girl with the rope hits the water first, as in the video. Or if the rope is being pulled off the bridge, that girl arrives second. Or if the rope is always entirely slack in the sense that it is dropped with the girl and the signal that it is attached at the other end never arrives at the girl, then they hit at the same time. So it is indeed interesting to consider all these possibilities.