It does still work.
The most suitable view to use is the playlist's Songs view:
- go into the Playlist and then tap on iTunes' top bar menu; View/View As/Songs
- to manually sort a Playlist, the arrow has to be in the "number" column (to the left of the tick box column) and that's achieved by clicking on box of that column header. Clicking that box a second time reverses the arrow (and the order of the list).
- the arrow can be either up or down.
- if it's up, any song that you add to the Playlist will be at the bottom of the list
- if the arrow is pointing down, new songs are added to the top of the list
- in the screenshot below, note the position of the song Awakening Spirits (position 28):
- simply click-and-drag the song to the new position in the playlist. As you move the song to a new position, a blue line appears between the two songs that you are about to drop it between
- notice that the song Awakening Spirits is now in position 26. Note the song Emerge is still in position 25 and the song Moonlight is still in position 29
- if the arrow is above any other column, you cannot move songs manually, because the column with the arrow is dictating which order the songs are in
If the blue line does not appear when you drag the song, then you do not have the "number" column selected. In the two screenshots below, notice the iTunes icon and the red circle with a 1 in it (there will also be a + icon, but that can't be captured in a screenshot). This triple icon appears when you drag a song to another position in the list .
- in the first screenshot below, notice the arrow in the "numbers" column (so the playlist is in "as added" order) and the blue line between numbers 25 and 26. This means that the song can be moved (from position 28 to position 26):
- in this second screenshot (below), the sort arrow is above the Name column, which means that songs are in alphabetical order and cannot be manually moved. When trying to drag a song you still see the triple icon, but the blue line is missing, which means that you cannot drag the song to a new position:
You may have noticed that I'm using a Smart Playlist in this demonstration, but manual sorting also works in Regular Playlists in exactly the same way.