From the section of your post that states your goal...
...at the moment I like to bundle CISCOs Presentation which I made its in CISCOs DMD, together into 1 playlist. So I can set inside my schedule for half day to loop mornings playlist. while another playlist handle in the afternoon.
my understanding is that you want one playlist to loop during half of the day, and another playlist to loop for the second half of the day.
You can do this by using the scheduler to scheduling your playlists for the times that you want. If scheduled time is longer than the playlist, the playlist will by default loop around.
-Hashir