Single Status Update
...after swearing I would never buy one. Specifically the new Nano.
I'm liking it so far, nice and easy to use. Its a shame Songbird no longer has a supported ipod plugin, so stuck using iTunes for syncing at the moment.
Am I hip yet?
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If you're looking for an alternative for iTunes, check out Exaile for Python (Windows should have a freely available Python Development Kit) or Amarok ... which isn't "officially supported" in Windows but it has a Windows binary available ... these apps require a libgpod plugin to work with an iPod, but it shouldn't be too much trouble to install.
As you can see by the links posted above, these are open source projects for GNU/Linux distributions (I use Amarok 2 in Mandriva myself and find it very convenient), but they should be easy enough to port into Windows.
I've been using SharePod, seems to do the trick.
I'll check those two out and see how it goes.