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I imported all of my music into my itunes library yesterday, but it didn't exactly go as smoothly as I wanted to. For directories that consisted of albums (like Coldplay - Viva La Vida), I just dragged each of them to the playlist area in itunes and it created static playlists for each of those directories. That was fine because I don't need them to be smart playlists - they're never going to change. However, I did run into some problems with my other directories.

For directories like Miscellaneous, Rap, Rock & Alternative, etc., I created smart playlists for each of them and created rules based off what was in the grouping field. The problem with that is that any songs I imported into my library that belonged in one of those smart playlists only went to one playlist For example, I imported my entire "Miscellaneous" directory and then did a bulk edit of those songs so that the word "Miscellaneous" appeared in the grouping field. That pushed each of those songs into my "Miscellaneous" smart playlist - great. The problem arose when I then tried to import my "Rock & Alternative" directory. If there was a song that was in my "Rock & Alternative" directory that had already been imported because it was in my "Miscellaneous" directory when I imported it, it did not get imported again. In theory this makes sense because you don't need two copies of the same song in your itunes library; however, now I need to figure out a way to determine which songs are supposed to exist in both my "Miscellaneous" playlist as well as my "Rock & Alternative" playlist. I can't figure out an easy way to do that. As it stands right now, I'm going to have to go through each of those smart playlists one by one to see which songs are missing from the corresponding directories that I imported.

If there was a way to convert a static playlist to a smart playlist, that might work but I couldn't find any way to do that. If any of this makes sense to anyone else but me, please feel free to make suggestions. Thanks!
 
Just add to the comments of the song. If one song should be in "slow songs" as well as "rock", just put that in the comments. Then make a smart playlist looking for "slow songs" and a smart playlist looking for "rock".
 
The way I'm doing it with the grouping field is basically the same as what you suggested. The problem I'm having is trying to figure out an easy way to identify which songs are supposed to be in multiple smart playlists and tagging them to make that happen.
 
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