I use iTunes on both my Mac and Windows machines here at work. On my Windows box, it's not quite as smooth and takes up a few too many resources, but I still run it to listen to music from other users on my network. On my Mac, it couldn't be better, but I've found that the biggest problem I have with iTunes is not with the program itself.
In fact, even though it's mostly my fault, my music library is what gives me the most trouble. Like most people, I've gotten my music from a number of different sources so a lot of music is tagged incorrectly. My cover art is almost nonexistent so I can forget about using Apple's fancy Cover Flow feature. Some songs I accidentally added more than once, while others are from mix CDs where a song might read "Track 8" so I don't even know what it is until I listen. Certainly, I could spend a day going through each track, switch the tags, and grab the cover art, but who wants to spend all day Saturday sifting through their music library? Not me.
Fortunately, someone has developed an app to fix this situation, though it is not yet perfect. TuneUp Companion from TuneUp Media is an iTunes plug-in that helps you analyze and clean up a messy library in a fraction of the time it would take to do manually. The TuneUp Companion interface shows up to the right of your iTunes music library with features for cleaning up tags, finding album artwork, getting more info about artists, and genre-related music recommendations. You can also search concert listings in your area for bands in your library.
But does it work? Obviously, the feature that really caught my attention was the Clean tool. It takes an audio fingerprint of a mislabeled song, matches it against Gracenote's Global Media Database of more than 90 million songs, and returns most likely matches, which you can save to your library. It even recognizes songs from the same album so you can get both music and cover art in one fell swoop. In my testing, it worked almost flawlessly as long as I only chose groups of 50 songs at a time, but simply selecting my library and trying to clean it all at once seemed to bring the program to a crawl. I have to admit, even if it's just a batch of songs at a time, TuneUp Companion made organizing my library a whole lot easier than tagging each song individually, but ideally it would be a one-shot operation.
TuneUp Companion's other tools worked great. The Cover Art tool quickly scanned my library and offered covers for every artist it recognized (my library has everything from regular songs to sound effects to music my friends make, so it would have no chance to recognize it all). The Now Playing section offered up music videos for the artist playing, a link to StubHub concert tickets, and similar artist recommendations from Amazon, all accessible with a click of a button. The Concerts section let me know where I could see acts locally for all the music in my library.
TuneUp Companion isn't perfect, but it's definitely a great start. The development team assured me updates were on the way to iron out the few bugs remaining and a Mac client is due in the fall (for now TuneUp Companion is Windows only). The trial version listed here at Download.com offers 500 "cleans" and 50 cover art "finds"--not nearly enough for most libraries. An unlimited version of TuneUp Companion costs $19.95 for a one-time charge or you can get an annual subscription for $11.95.
Overall, I think that though TuneUp Companion was limited by how many songs it could clean at once, it did a great job of properly tagging my music library. If you try it out, be warned it will take some time processing groups of songs from bigger libraries, but with what I've seen so far, this is a giant leap for iTunes users who have been looking for a way to fix their listings (almost) automatically.