The name seems daft, but this Windows Media Player ("WMP") 11 plug-in seems promising. I've long been a WMP fan. I only use iTunes because it was the only reasonable way to manage music on my iPod – until now. Microsoft chose, once again, not to provide iPod support in its latest version of WMP. To the rescue comes MGTEK with DOPISP. DOPISP is a plug-in for WMP that enables you to sync your MP3 music to your iPod directly from within Windows Media Player.
A free two month trial is available here. No word yet on final pricing. Of course it cannot manage any DRM'd AAC files purchased from iTunes. If it could, my work here would be done! Well, at least until Apple and/or the RIAA sued them! 🙂
I haven't tried it yet, but one possible downside to this approach to managing your iPod is that it likely won't support podcasts. For some reason that only the God's know, Windows Media Player does not include podcast support. Since I discovered podcasts in October of 2005, I use my iPod primarily for podcast listening while on the road. Without podcast functionality, I'm not ready to head back to WMP!