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iTunes

what format are you ripping to?
what quality are you ripping to?
do you have error correction on?

more over, why are you ripping the same cd twice?
I never used itunes until just recently, and even still I'm not knowledgable about this sort of thing, so I can't answer the first 3 questions; although one of them is probably the answer.

As for the 4th question, my comp had kind of a meltdown recently, so I have to re-rip all my music, and I figured since I have an ipod now I should use itunes.
 
Just don't use iTunes on a PC. It runs like crap and hogs a ton of resources. Winamp can synch to ipods just as well as iTunes, and it doesn't run like crap. You can also rip in winamp, straight to high quality MP3, or even FLAC or OGG.
 
Just got an iPhone 3G yesterday. I couldn't run any of the 3rd party apps that I installed and Safari was shutting down on me. Turns out its a widespread problem (all over the macrumors forum) having something to do with how itunes handles DRM. Supposedly there will be a fix out Tuesday but until then I had to roll back to an older version of itunes and that worked.

Aside from that problem I also don't really care so much for the itunes interface or the itunes store layout. Playback of identical files does sound better than WMP when doing an A/B though.

bc