There are some things that Apple makes easy, and others that stay complicated. If you have more than one computer – especially if you have Mac and Windows – handling backup and synchronization is a pain.
I use a Windows machine mostly as a media player at home, and a MacBook for work and mobility. I had most of the iTunes library on the Windows machine, and a few things that I had bought on impulse while using the Mac. I wanted to use the Windows machine (an XP laptop with a busted battery and some Logitech speakers) as the main media player (because I own it), and the mac for sometime listening. I wanted it all backed up, ideally in a couple of places, and I had a 300G USB hard drive for backup.
Here’s what I needed to do:
* locate and import some missing backup files from a dead computer into the main collection (the key was to search for a distinctive song title)
* reformat the hard drive to FAT32 so that it could be read/written from Windows and Mac. It had been formatted so that Windows could read/write but Mac couldn’t write.
* use the external hard drive to move the Mac library onto the PC laptop
* carefully copy the Mac files into the PC folders (there were a few artists for whom I had different albums on each)
* turn on “Sharing” for the windows machine so I can listen at home
This multi-step process took a little bit of figuring out, with the help of Google and some nice folk at the Apple store. Once I figured out the steps, the implementation took a few hours but was pretty straightforward.
I signed up for an online backup service, but didn’t use it because it seems like it will take a few days to back up my collection and that’s not practical. To make a second backup that’s not in my house, the way to go seems like a USB keychain that lives in my bag or wallet. I’ll rip some CDs and see what size I need.
As the next step in the project, I’ll become the last person on the digital planet to RIP my CDs. Why am I only now getting around to ripping CDs and organizing a digital music collection? To make a long story short, I hadn’t taken care of the digital music collection because until Apple and the labels took off DRM I considered the digital stuff disposable, and bought as little DRM’d music as I could. I had spent the time in Austin mostly focusing on Austin music, mostly on CD. When I got to the Bay Area, I was heads down on work for a bit.
When I came up for air, I wanted to “true up” my music collection and taste; I didn’t want to just listen to the things I already liked and things that are nearly identical. So I’ve been doing a little exploring with the help of last.fm and youtube and wikipedia. That’s a longer story that may or may not make it to blog form.
As you might expect, I’ve taken a Linux-centric strategy in my approach to this problem. I use rsync to move digital music files around, including to portable music players. The only difficulty there is that it really wants to synchronize the stores completely, and my MP3 collection is about to overflow my 60GB player.
For more directed sync (e.g. a documents directory) I like Unison.
http://www.cis.upenn.edu/~bcpierce/unison/
And all this is probably no help to you whatsoever…