Until recently, I've hardly seen the appeal of Apple's iTunes. Being a Windows user since my first home desktop, I've always been accustomed to listening to mp3's and music in general with Windows Media Player. Everyone has their opinions on which player/OS is best but I'd made my choice simply because it was what was on my computer. Over the last 10 years or so I've compiled a pretty extensive collection of music. Some of it being from the early days of mp3s, even, and much more still from a tonne of ripped CDs I still have sitting on a shelf. Within Media Player, I'd gone so far as to start rating most of my tracks. You know, those 5-stars your see in the library that nobody uses. I'd also started making auto playlists to make those high rated songs easy to find. And then, around the end of 2008, I finally got an iPod Touch.
Catastrophe! I had basically no choice but to download iTunes and find some way of transferring my (somewhat obsessively) organized Media Player library. My initial solution came down to this: 1) Select all songs in my "top rated" smart playlist, copy them into a regular playlist and save it as an m3u file, 2) Remove all songs that might be in the iTunes library and then import the m3u file to iTunes, thus bringing in all my "good" songs. Now when syncing the iPod I would select that one imported playlist.
I won't be insulted if you have a palm placed squared against your face at this point, I know I do. The biggest problem I had with making the switch was a nagging problem I've tended to have with all of Apple's software, relinquishing control. With Media Player I'd gotten used to being able to make changes to music files directly (such as change the filename), and those changes would show up in the library without any fuss. If you do this to iTunes, it just marks the song in the library with an '!' and leaves it up to you to sort out the mess you've made. It's taken me nearly 3 years to come to terms with this....
The biggest issue with making the switch, however, came down to the track ratings. At the time there was simply no way to convert media player song rating to iTunes ratings. To get a bit technical, Media Player gives two options for storing ratings. The default, like iTunes, is to keep the ratings in a database. If you lose this database, all the ratings are lost as well. The second option is to store the Media Player rating as an ID3 tag within the file itself. ID3 tags are simply bits of "meta-data" that contain information about the song, like title, artist, album, length, and whatever else you might want to know about a track. In this case, if the database is lost, the ratings are safely stored within the music files themselves and are easily recovered. iTunes, on the other hand, only allows ratings to be stored within its library database.
About a month ago I finally found my saviour. On a personal programming/project blog, here, was a little piece of software called Orzeszek Ratings. Granted I haven't looked too deep into its inner workings, it works by accessing the Media Player and iTunes API's to match tracks that appear in both programs, and "translate" ratings from one to the other. This was basically the last hurdle for me to let iTunes into my life for good.
So now, for the sake of the iPhone 4 I bought 3 months ago, I'm entirely managing my music through iTunes. There are a couple things that still nag at the back of my head though. If the iTunes database/library files get corrupted or lost, then all my ratings, playlists, etc. are gone. I'm no fool, of course, I do regular back ups of music, photos, work, and all that bric-a-brac. So, in theory, if iTunes breaks, all I have to do is copy the backup files and all should be good. I hope I never have to test that theory.
I'll wrap up with some actual praise for iTunes for a change, especially recently. First off, subscribing to podcasts and the interface for syncing with the iPhone/iPod is very slick. I can hardly think of easier ways of doing it. Changing the music you put on it or the organization of apps is hardly more than a couple mouse clicks. If I buy a new song and rate it highly, it'll automatically appear on the high rated smart playlist and then, since that playlist is selected for syncing, will automatically copy to the iPhone. Second, the newer Home Sharing feature Apple added is very nice. Sharing existed before in the form of being able to access and play other people's shared iTunes library's. Home Sharing, however, depends on you entering your Apple/iTunes account information. Doing this means that you can not only play the music on a shared library but also COPY songs into your local iTunes library, as well as automatically download new purchases. I now can't see myself going back to Media Player.
Now, the next hurdle will be to enable the "Let iTunes keep your files organized" check box....