iTunes organization: making the most of a large library
The Unofficial Apple Weblog has a great article on how to organize your iTunes library, just in time for their readers' New Year's Resolutions. It's a wonderful set of suggestions, but I'm not seeing how they'll work for me.

Most people who use iTunes have probably put some effort into organizing their iTunes Library. What makes me different, perhaps, are a few characteristics: I'm using iTunes to organize not only multiple users (Karsten and myself) and multiple media (music, movies, etc) just like everyone else, but I'm also using it to organize both business and pleasure. I acquire a lot of music that isn't for my listening pleasure; it's for songwriting research. Believe me, I'm not a big fan of certain war-mongering politically-über-conservative country artists I could name, but I have copies of most of their CDs anyway. It's important to me to be familiar with what's getting sales and radio play, even as Karsten and I strive to bring our own style to pop country songwriting. Anyway, all that means that I have a huge passive library of music on my external hard drive.

So here's what I do.

Metadata Metadata Metadata

For each new CD I get, I use the Sing that iTune! widget on my Dashboard to dig up the lyrics for each song (or at least each radio release I know of) as it plays and let it automatically populate the Lyrics tab of the song. I make sure to enter the songwriter info off of the jewel case insert before I sell it (or return it, if it's borrowed). I use the comments field extensively in each song file as a place for keywords, and these can include songwriting concepts like "bigchorus" or "aaba" as well as thematic elements like "mellow" or "loveassalvation." I have smart playlists set up to look in the lyrics and/or comments fields and pull out groups of songs under headings like "themes: i can't get over you."

Since these are all smart playlists and therefore dynamically updated, I don't have to worry about losing playlist relationships when I delete and re-add songs to and from my library.

So at any time, I may be working on a concept having to do with, say, rain. I can plug in my external hard drive, search for "rain" and drag all those songs over into iTunes. Since I've focused my efforts on being able to bring songs from my external hard drive into my local library and have them immediately fall into place where they belong, I immediately have a full playlist of reference material for "songs about rain."

Play Counts & Ratings

Like many people who depend on iTunes, I have had multiple losses of play counts and ratings. What I've learned from those experiences is to give up, for the most part, on the play counts, but preserve ratings in a different way. I now use the comments section of the song file for keywords. One of the keywords I use corresponds to how many stars I rate the song. For instance, "5star" songs should all have, duh, five stars.

Then I have smart playlists under a folder called "qa." Every so often I go in and clean up a bunch of modified songs. There's a set of smart playlists for songs that have a certain star rating but the comment doesn't match (if I've rated them but haven't updated the comments), and a set of smart playlists for songs that have a certain comment rating but the stars don't match (if I've re-imported them from my external hard drive and haven't updated the rating). Since I can select a bunch of songs at once and mass-update them, this whole process takes under 2 minutes every few weeks.

Backing It Up

The part I haven't figured out how to streamline yet is getting modified files backed up to my external hard drive. If I imported a few songs and made changes to their keywords while they were local, I'll naturally want to save those changes when I back them up. But I've yet to find a good backup program that will look at what's changed in my local iTunes Music folder and copy it to the corresponding location on my external hard drive's iTunes Music folder. I've tried creating an Automator workflow with the Backup Folder action to do it for me, but it's dealing with such a huge set of data that it hangs. Suggestions appreciated.

For now, I rely on manual copying. Sure it's tedious as hell, but this is a huge investment for me and I want to make sure it's right.

So what are your methods? What do you do to make sure your music collection (whether in iTunes or not) is organized the way you need it and backed up properly?