1v@n wrote:
I see the discussion is about smart playlists.
Correct, it is. And that's the point. If you notice, micarta, who set that question was experiencing the same issue as you. Namely, that the same few songs were being played too often in the shuffle list.
Try this - it's really easy and will take you all of three minutes to set up (less time than it's taken me to type this!)
Create a Smart Playlist (it's that very large + button in the bottom left corner of the iTunes window). Let's assume for now, that your 2,000 song standard playlist is named 2000 songs and that you listen to approximately 10 songs on each journey (so 20 songs per day, five days a week). That's 100 songs per week and in 15 weeks, that's 1,500 songs. Don't get hung up on the arithmetic, you don't need to remember it and it will make sense in a minute.
Your Smart Playlist rules should look like this;

In my particular example, both of my lists will have the same number of songs because I'm simply making up my list (which you'll notice only has nine songs, not 2,000. 😉 ) You don't need to have your 2000 song Playlist highlighted, as I have, when creating the Smart one.
- Clicking on the arrows will show the drop-down menus, from which you make your choices.
- The Match / all at the top will only change to that when you select the second rule.
- Create a second rule by clicking on the + button at the end of the first rule's line.
- Do not select the Limit to box, you don't need it in this set up.
- Do select the Match only ticked items, it will stop songs that are not on the iPod but in your Library from showing up in the iTunes version of the list.
- Leave Live updating selected.
What you then have is the Smart Playlist, which I'll name Work Journey. The only songs in it will be songs that have not been played for 15 weeks. So if you have played - let's say - 450 songs, that are in your standard playlist, in the last 15 weeks, the Work Journey Playlist will only have 2000-450=1550 songs. The other 450 will not be there. So when you play from the Work Journey Playlist, it simply cannot play anything that has been played recently (surprise surprise, 15 weeks!) As each work day passes, the Work Journey Playlist has less songs in it - until - songs that have not been played for 15 weeks, are put back into the Work Journey Playlist and can be shuffled for play in it. So after a while, the playlist continues to have roughly the same number of songs in it, they're just different songs.
Based on my arithmetic, your Work Journey Playlist should never run out of songs. But if it should (perhaps because you've played some of the songs at another time and from the Album or Songs menus), then all you need to do is reduce the number of weeks in the rules of the Playlist (highlight the Work Journey Playlist and select File/Edit Smart Playlist).
There was one further thing. You believed that some songs in your standard playlist were being skipped. If a song is marked as Skip when shuffling, then it will be in the Work Journey Playlist but it will not be played in shuffle mode. You can spot if there are any.
In the 2000 songs Playlist and on your iPod, set the Playlist to play in normal mode and start with the first song in the list. On the Now Playing screen, you will see 1 of 2000 displayed, where 2000 is the number of songs in the Playlist. Before that song finishes playing, change the iPod to shuffle mode with the shuffle icon in the top right of the Now Playing screen. If the 2000 changes to a lower number, you have songs in the Playlist that are set to Skip when shuffling. All you need to do is find them.
In iTunes, highlight a song and look on File/Get Info/Options>Skip when shuffling.
Let me know how you get on.
Message was edited by: the fiend