Create your playlist. Then on the schedule tab, set your show dates. Then add your playlist to the schedule. At the bottom of the "Schedule Playlist" window will be a list of all of your show dates. Simply click on the first date to select it, then scroll to the bottom of the list and shift-click on the last date - this will select all of the dates. When you click OK, then playlist will show up under every date of your show schedule.
If you've already scheduled your playlist for one day, then you can activate it for all days by clicking on the playlist in the schedule to select it, then click "Update Selected Items", then proceed as above.
Matt
