So, I realized that I had a whole bunch of garbage music in my collection and decided that I really wanted to get rid of the crap and keep the good stuff. I needed a way to do this methodically. iTunes has a couple of great ways you can do this: Play Count, by Genre, by unclicking songs, etc.
First things first, I had about 10GB of duplicates, so I used their duplicate finder and deleted all but one of every single song that showed up. It was easily 10GB of duplicates. This was a small victory, because I got rid of so much junk, but I still had something like 39 days of music left.
Next, I scanned through by artist name and just outright deleted everything I knew I would never have a desire or reason to listen to again. Sorry Jazz genre and everything by No Doubt/Brittany/et. al. This got rid of another couple of Gigs of data. Empty trash, another small victory.
The best idea I could come up with next was to just organize by genre and start un-checking the box next to every song if I liked it, deleting the song if I hated it. This worked for a while. I got down to 29 days of left-to-check music. That felt really good, until I tried to add my playlists to my iPhone and realized that songs with un-checked boxes get left out of playlists. Also, genius will avoid those unchecked songs so my genius playlists all sucked. Hard.
Then I realized what I had to do. I created a playlist called “filter these” and added everything that I had not listened to yet. Any time I want to keep the music, I just delete it from the playlist. This avoids the whole “are you sure you want to delete?” and then the “confirm you are really really sure” messages, saving me more time. Also, if I want to delete the song from my library I can’t delete it from the playlist, because its still in the library. So, what I do is un-check the box. This un-checks the box in the library, which means that I never listen to that crap again. Also, it is uber-easy to find so I can mass-delete the whole lot of garbage at once.
I have been flying through sorting my music. I now have 14.2 days left in my playlist and only 19days total playtime in my whole library. Now that feels really good.