iTunes v5.0 Redux 

I ended up spending a few hours yesterday cleaning up my iTunes library. Basically, when I first starting using iTunes (a couple of years ago), I didn't want it to control which songs it would sync to my iPod. I wanted control over that.

A couple of years pass and now my two libraries (the iPod and iTunes) are out of sync. When you manually update, iTunes doesn't bring play counts and last played data back from the iPod, so you lose some of the cool smart playlist abilities. It's bugged me for a while, almost to the point of writing a Perl script to update the data myself each time the iPod sync'd.

Instead, I figured I'd just spend some time merging my libraries. I started with CopyPod, which lets you merge your iPod library (play counts, ratings, etc.) back into iTunes. This, however, left me with an entire duplicate library. Thankfully, I could just sort by date added. Boom, dumped all the duplicates, leaving myself with a merged library.

How to control what songs sync to my iPod? I created a playlist called iPod Songs. This playlist contains all of the songs I want sync'd out to my iPod. Now, if I want to make a smart playlist that will work on my iPod, I just make sure it includes a criteria that the song exists on the iPod Songs playlist. Surprisingly, it works really well.

Finally, I figured I'd add album art in to iTunes. Found this nice app that will do it automagically by going out to Amazon and downloading the album art. It made a few mistakes, but 30 minutes of work cleaned that up.

So now I've got a single library, with both my normal iPod and my iPod Shuffle updating play counts. Now I can start adding some older CDs in and building out one big library, which was the plan all along.

The point: iTunes made all of this a pain, but once you get things working sort of the way iTunes likes it, it's a really good application. I'm a much bigger fan of the new interface and some of the abilities it has (playlist folders, particularly).