So I got an iPod about a year ago now. Black 80GB Video 5.5Gen. I'd heard many, many stories of the horrors of iTunes and the DRM it gives you. Thus, my iPod has never touched iTunes. I use Winamp, but I found a much better plugin for iPod support than that offered in Winamp. My iPod has never touched iTunes.
When we got the Mac, we were planning the whole time to use Parallels so we wouldn't have to leave anything behind. Well, I've begun to sever all my ties with Windows. There were four main things holding me back:
-Google Talk (iChat and other solutions to be written about later)
-Microsoft Office (solution to be written about later)
I know games can never be transferred to Mac (a conversation to continue at a later time), but I've found solutions for Google Talk in Audium, Microsoft Office in OpenOffice.org, but Winamp?
I've done some research out there for other media player, but honestly, none of them really looked worth it. The closest one was Songbird, but it just didn't look that tempting. Winamp has pretty resolutely stated that they will never make a version for Macintosh, so I've pretty much given up all hope of that.
As such, I've swallowed my pride and resigned myself to iTunes. I still have no plans of ever using it with my iPod, (I'm paranoid enough about the auto-detection that I only use it via BootCamp). We'll have to see how this story develops over time.