I was lamenting the other day about stereo configurations and alluded to my ever ending struggle to manage my iTunes library across several laptops, external hard drives, iPods, etc and how no matter what I do I can never get them synced the way I want them to be. I started asking a few people how they handle their own set ups to try and get some ideas on what might work better and I think I have a new solution in sight. I have to give credit to Jason Carlin for some of the concept here as I’m following his lead on a good bit of it.

My problem, which has frustrated me to no end, was trying to have everything synced up, and with me, and accessible, at all times. I should have applied my “just let go” concept of the rest of my life to this as well but didn’t. My new plan, is forget about syncing it all – break it. I’ll explain.

Thanks to Simplify Media I can not only access a small handful of friends iTunes libraries from anywhere I have a web connection, but I can also access my own libraries. See where this is headed? As long as I have a machine that is always on, and always online, I don’t need to drag everything with me all the time. Of course there are some things I want with me all the time in case I need them when I don’t have a web connection, or if I want to let friends check them out. This is where Jason’s suggestion of multiple libraries suddenly makes so much sense.

There is a good chunk of my MP3 collection that I never want to get rid of, however it’s not something I listen to regularly. Friends bands from college, audio books, kitchy theme albums, etc – things that are great to have and pull out when needed but don’t need 24/7 access too. This is where the massive home library comes into play. Home computer + web connection and bingo I can listen to any of that stuff any time I need.

Then comes the issue of breaking the library from that stuff, older archives, and newer listen-to-it-a-lot kind of things. That’s really just going to take some sorting by hand but it shouldn’t be too much of a pain. The newer stuff I can keep with my on my laptop (which is also connected so I can access it at home too) and gives me access to those files when I need them. My main concern with this is making sure that some of the data in those two iTunes libraries isn’t lost such as playcounts and things, which brings me to my next point.

For the first time in my life I was considering an iPod that held my entire connection now that there are finally some big enough, but then I started thinking about the above stuff why do I need some of that stuff with me, which I felt meant endless amounts of sorting. Jason told me that he has one giant playlist of anything he’s gotten since some date that he syncs to his iPod so he always has the stuff he’s interested in listening to with him. I already use smart playlists quite a bit and thought a tweek on this might be really good. A few of the smart playlists I already use are New & Loved (Added within last X days, play count more than Y, skip count less than Z) as well as New & Unheard (Added within last X days, play count less than Y, skip count less than Z) and some of the more common things like songs that have been played more then 25 times, etc.

I decided to make a list of songs that have been added since Jan 1 2007 with a play count of more than 1, skip count of less than 1, genre that isn’t books or lectures, and a few other things and coupled it with some of the above lists. I auto sync those to my iPod and suddenly instead of 80GB+ of everything I have, now I have something closer to 12GB of stuff I listen to all the time. It’s going to need some tweeking, I can tell that already, but I think this is the right direction to manage this stuff.