Moved from PC to Mac cannot transfer songs to ipod

I have a 20GB Click Wheel ipod which I have been using on a PC with XP. I have now moved to a Mac G4. I have downloaded itunes 7 and loaded my songs via back up discs on the Mac and sorted my playlists. When I try to synch my ipod no playlists or songs transfer although itunes does find my ipod. My ipod is formatted for Windows but apparently that should not make difference.
On reading I have seen that anything bigger than 4GB's won't transfer. I have 1,503 tunes in various playlists totalling 6.03GB. If I compress my library as suggested it will not only take forever but I will then have 2 copies of each track plus I am not sure if it will compress it enough to synch.
I have tried restoreing my ipod to factory settings but get a message saying: 'cannot be restored because it contains files that are in use by another application'.
Short of buying an new ipod which I cannot afford has anyone any ideas how I can synce my ipod?

Hope the following helps, otherwise, it can be a bad hard drive
For Mac computer
1. Open the disk utility, hope your iPod appears there (left hand side), highlight it
2. Go to Tab “Partition”, click either “Delete” or “Partition”, if fails, skip this step and go to 3
3. Go to Tab “Erase” , choose Volume Format as “MAC OS Extended (Journaled), and click Erase, again if fails, skip it and go to 4
4. Same as step 3, but open the “Security Options....” and choose “Zero Out Data” before click Erase. It will take 1 to 2 hours to complete.
5. Eject your iPod and do a Reset
6. Open the iTunes 7 and click “Restore”

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www.paragon-software.com
Some general Apple Help www.apple.com/support/
Also,
Mac OS X Help
http://www.apple.com/support/macbasics/
Isolating Issues in Mac OS
http://support.apple.com/kb/TS1388
https://www.apple.com/support/osx/
https://www.apple.com/support/quickassist/
http://www.apple.com/support/mac101/help/
http://www.apple.com/support/mac101/tour/
Get Help with your Product
http://docs.info.apple.com/article.html?artnum=304725
Apple Mac App Store
https://discussions.apple.com/community/mac_app_store/using_mac_apple_store
How to Buy Mac OS X Mountain Lion/Lion
http://www.apple.com/osx/how-to-upgrade/
TimeMachine 101
https://support.apple.com/kb/HT1427
http://www.apple.com/support/timemachine
Mac OS X Community
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Moved from PC to Mac cannot transfer songs to ipod

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