Could you cite how many occasions this 'happened to you' in the course of your duties?
Never!
Not only "never" but in the area I worked in I cannot remember a single instance of a siding/crossover set up as in the illustration!
We had plenty of switchlocked sidings in double line areas which needed a crossover, but the sidings were generally substantial involving AT LEAST two roads with points at each end to allow for running around wagons, even if there was only one set of points joining the sidings to the main. In those cases both up and down trains could shunt quite happily.
And yes, our signals were inevitably interlocked with any crossing alarms that might be needed but our disc shunt signals only ever indicated that "the points were correctly set for the movement which was now authorised but that the track was not necessarily unoccupied." This meant that one disc would suffice for any number of alternate routes as the driver had to move under shunting staff direction or at the very least at such a speed as to be able to stop clear of any obstruction (what we used to call the "company rule"). In the event the majority of our signals were colourlight ones and only one ground shunt signal would be provided for any number of different route settings. You Victorians obviously took route signalling seriously. The closest we would come to that would be using a three position ground shunt which would only ever show a green when the route was set for the main line and there were mainline signals further along; all other movements would be indicated by a yellow.
Cheers
Nix