Very simple: it should be possible to add an item to a playlist multiple times if desired. That would make them work more like playlists in other music apps. There’s a number of reasons a user might want to repeat a track or movie, and it would be great if we had the ability to do that.
I would also like to see this feature added, with a “This file already exists in your playlist, do you want to add it again?” confirmation similar to other media playlist management apps.
Upvoting this. Being able to repeat the same item, either multiple times or just within the same playlist would be hugely valuable.