Belated spring cleaning, iTunes style

According to iTunes, I have 2879 items taking up 14.21GB in my iTunes library. Sadly, this is about five times as much free space as I have on my iPhone, which spells T-R-O-U-B-L-E for my plan to ditch my existing iPod. However, I hit on a useful strategy. I already have a playlist called “Never Played”, currently at about 2056 items. This is a little misleading, since I’ve actually played many of those songs between flattening my iPod, moving my music library, and so on. However, I now have a new rule. I have to listen only to that playlist. Any time I get the urge to skip a song, or find a song that I haven’t heard and don’t like, IT MUST GO. We’ll see how well this works to weed out stuff I wouldn’t listen to anyway.