My iPod is Full

My 40GB 3rd generation iPod has been on the verge of full for awhile but now it’s solidly in ‘full-land’. I added pretty high quality cover art to a bunch of my albums the other day using Corripio and that added almost 1GB to my iTunes library. I have the iPod set to sync automatically (managing it manually is not an option) and to skip unchecked songs so I had just been unchecking albums I rarely or never listen to up to now. I’m pretty much out of the obvious choices now, though. I don’t actually listen to the majority of my digital music library on a regular basis but I love the idea that I could.

So now I’m at the point of trying to figure out how to choose the 37GB or so (that’s how much music actually fits on a 40GB iPod) of my music that covers everything I’m most likely to want to listen to at any random moment. I think when I buy a new iPod I’ll probably go for a slimmer model with a smaller drive so for the next few revisions this size drive is likely to be the largest I’ll have.

I started by created a new smart playlist that was everything rated 3 stars or higher, or not rated at all (ie, no 1 or 2 star tracks) and I thought I was in luck when that turned out to be just over 37GB but for some reason it was still too big. I ended up setting a few Orbital albums that I seem to never want to hear (I guess I heard them too much in college) to 2 stars so they would not be included. That worked, but now it bugs me that the ratings are not really ‘accurate’. A little crazy, I know. I could have just unchecked them (and I may) but then they would never get played at all since I’m very unlikely to seek them out. I feel like I should be able to come up with a smarter way.

I already have several ‘self-modifying’ smart playlists (basically, a track will be taken off of the playlist when it’s played and then randomly show up again later) that I listen to when I don’t feel like picking what to listen to so I might be able to use one or more of those as a basis. I would also, of course, always want to have my most recent library additions included. That is, unless I somehow mark it so it won’t be included. I want to try to make sure I’m never missing a song I want to listen to but also somehow try to make sure my iPod playlist never goes over 37 or so GB, as well. Maybe some sort of system based on play count combined with date added to the library so tracks I find myself never listening to eventually go stale and disappear? Unfortunately I do occasionally lose an album and forget to listen to it and it’d be a shame to have those end up gone forever. It’s all so complicated!

So, at this point the iPod is full and is missing some Orbital that I don’t really ever choose to listen to along with other albums I just keep around to be able to say I have (or something). The manual management of the whole thing is driving me crazy.

UPDATE: I came up with a pretty good full iPod strategy. You might like it, too.