Do I need to wait for a file to finish optimising before adding it to the playlist?
No. Even if the file is still being optimised, you can add it to the playlist as usual.
Why the file may appear on the TV before the optimisation finishes
While the original file you uploaded is being optimised, Adeus Pendrive also optimises the file for display on each TV.
That is why the file sometimes appears on the TV even before the optimisation of the original file finishes.