Smart playlists not updating live after 3.1.1 upgrade

Question

Same discussion started back in February about the 3.0 update (http://discussions.apple.com/message.jspa?messageID=9937797)
I thought for sure live updating would work properly with such an update from 3.0 -> 3.1.1, but no luck! I guess it takes more than 7 months to fix this.
As a refresher -- if you have a smart playlist that includes a "not played in the last xx days" condition, the old OS (2.2.1) would automatically remove a played song from the smart playlist on the iPod so your playlist is always valid. However, in 3.0 and 3.1.1, the iPod does not automatically recalculate the smart playlist and you have to sync with iTunes to get the song to be removed.

Answer 1

I have discovered a workaround for this issue. As with most workarounds, it's not too pretty, but it gets you there.
Knowing that live updating smart playlists that refer to other playlists won't properly update on the iPod, and taking advantage of the fact that iTunes 9 now allows for nested logic in smart playlists, we can make a complex nested logic smart playlist that live updates on the iPod as long as it doesn't refer to another playlist. In place of referring to another playlist, refer to some metadata instead. The cleanest metadata tag in my opinion is "Category." It is metadata that does not by default display in playlist view (you can enable it under the View menu), and is not visible when selecting Get Info on a track. You can use the excellent "Enter Category Text for Selected v1.1" script to enter Category tags, available at http://dougscripts.com/itunes/scripts/ss.php?sp=entercategorytext . Just enter the name of the playlist the track is contained in for the Category tag.
I'll give an example of how this works. Let's say you have a long playlist named "day" containing certain tracks you like to listen to when the sun is out. You want to create an intelligent and self-updating megamix playlist of tracks only from the "day" playlist that will play songs you haven't heard, as well as songs you've heard and have rated. As an added smartness, you want to hear the tracks you've rated higher more often than the tracks with a lower rating. You want this new "day mix" playlist to live update properly on your iPod touch.
First you'll need to tag all your "day" playlist songs. Download and install the "Enter Category Text for Selected v1.1" script mentioned above. Select all the songs in the "day" playlist, run the script, and enter "day" for the Category.
Now you can make the smart playlist. In iTunes 9, create a new Smart Playlist. Using the new nested logic in iTunes 9 smart playlists, select the following conditions:
) Match any of the following rules:
) all of the following rules:
) Category contains day
) Playcount is 0
) all of the following rules:
) Category contains day
) Rating is *
) Last Played is not in the last 6 months
) all of the following rules:
) Category contains day
) Rating is **
) Last Played is not in the last 5 months
) all of the following rules:
) Category contains day
) Rating is *
) Last Played is not in the last 4 months
) all of the following rules:
) Category contains day
) Rating is **
) Last Played is not in the last 3 months
) all of the following rules:
) Category contains day
) Rating is ***
) Last Played is not in the last 2 months
) Live updating
You should find that the new "day mix" smart playlist properly live updates on your iPod touch.
As with any workaround, there are troubling aspects. One is that you'll need to constantly update your metadata tag of choice (Category, in my example) each time you add new tracks to a source regular playlist on your iPod. I'm also unsure about overloading the metadata with a number of tags in the case where tracks co-exist on multiple playlists. Also be aware that smart playlists like this tend to hang the iPod for several minutes with the "Updating Library" screen, so be prepared to be patient.
I hope this is of use to someone. Please post any streamlining suggestions for this workaround.