A couple of posts ago I mentioned that I had switched to a subscription-based music service (Yahoo! Music Unlimited) from my typical setup of iPod + iTunes that I had been using for a few years.  During those few years that I used iTunes, I collected a decent amount of music in my library...about 4,000 songs.  These 4,000 songs were meticulously categorized, sorted, tagged, and rated, such that it was very easy for my to make Smart Playlists of, say:  every Ben Folds song that I haven't listened to in the past two weeks that I rated greater than 3 stars.

This ability to sort your music easily was the killer feature of iTunes for me.  The star ratings added real personality to my music collection, and allowed me to enjoy music listening more--my collection didn't just have to be on "Random Play All" all of the time.

When I switched to Yahoo, I found most of the music that I had really liked that already existed in my iTunes collection very quickly.  I downloaded them, and they were nicely tagged.  Unfortunately, this was a largely manual process.  I spent a couple of nights doing searches and adding albums to my music collection through Yahoo's slow (and often buggy) interface.  This process was so painful that the thought of migrating away from Yahoo--to Napster, Rhapsody, or even back to iTunes--gives me a headache.

The truth is that my playlists were better in iTunes.  Why?  Because of all of the metadata iTunes had collected about my listening habits.  Here's my contention:  I'd rather lose all of my MP3 files than that one iTunes file that contains my ratings and listening habits.  Why?  The files can be replaced...it's just a matter of time until migration tools are written that programmatically allow you to re-download your entire iTunes library in a subscription service.  In fact, it blows my mind this doesn't already exist.  But recreating my listening habits and ratings for each music file is an impossible task.  I'd have to start from scratch, and it would never be the same.

So, this brings up one final question as I continue to try and figure out the "optimal" music solution for me:  does anyone know of an application that programmatically reads an iTunes library file and helps you migrate to a new service?