For big playlists, it gets very time consuming trying to sort them by artist. doing this manually is extremely time consuming so it would be great if there was an option to let the program automatically sort a playlist by artist name, followed by album name (or year), and then track number (or name).
I also found an issue when i try to sort my music by clicking the header bar, it doesn't always put everything together from one artist, or it ignores part of the files. I don't know exactly what's going on but it's frustrating. This is the only free software that still works on old iPods, so I would be forever grateful if you are still willing to update it!