No, it happens automatically if you sort the playlist it by "Last Played" before you play it each time. You don't have to touch it again until next time.
I'm not sure what you're talking about. I'm glad it is working for you, but I suspect you misunderstand something fundamental about the way MC's Playing Now lists work.
Files in ordered Playlists do not move unless you do something to move them. You can drag them up and down to re-order them, or sort them using one of the column headers. Sorts using column headers are only temporary until you leave the view or refresh it.
If you sort a Playlist using a column header, and then play it (by double-clicking one of the files or whatever), the contents of the Playlist as they're displayed on screen at that exact moment are sent to the Playing Now list. But the Playlist itself
retains its original order unless you update the sequence by clicking the
Update Order button. Here's an example:
* I created an ordered Playlist called "Test. It contains 20 files that haven't been played in a while, but they're sorted randomly.
* I open a split view in MC so you can see the contents of Playing Now, which is initially blank.
* I sort the Playlist, so that the least-most-recently-played track is on top, and then play it.
* Playing Now is filled with the list of files as they looked when I played them (with the least-most-recently-played tracks on top)
* I skip ahead in the track so it completes playback.
* The track that just finished playing
doesn't move anywhere in either list (the Playing Now list, or the Test Playlist). Playback advances to the next track in the Playing Now list. The two match because I haven't refreshed the Playlist's view or resorted it.
* The track that already played won't ever play again because playback is "past" that one in the Playing Now list.
* If I re-sort the Playlist, then the played track moves to the bottom of the list, but I have to do this manually, and this change has no impact on the Playing Now list.
* If I refresh the Playlist's view, then it goes back to its original ordered (shuffled) state.
That's how it works, and that's how it has always worked. Watch:
MC20 - Playlist Order Example