A different angle.
Why try to convert iTunes whatever to whatever else?
Back when I had an iPod, I used iTunes (Windows) to configure it to appear as a normal drive, then completely removed the crapware suite it installed.
From what I've read, iTunes Mac is halfway ok compared to the windows abortion, but either way, ANYTHING else is superior to iTunes anything.
Mind you, "anything" else (and I've tried a few) wasn't fun to deal with, varying from just plain OK to downright painful, but either way, it was better than iTunes which was completely friggin useless.
With half a brain and careful manipulation of ID3 tags, transfers worked out quite well.
Both ways too, none of this never extracting from the iPod ever again bullshit.
And just so this isn't an anti-apple thing, Windows media player is up to version 12, and still a complete abortion. What is it with media player/managers? Can no-one get it right?