Mac to Windows, taking iTunes with me?

Switching from OS 10.4.9 to Windows Vista (tired of cross-platform issues at the office). How do I transfer my library from the G4 to the PC? If I sync my iPod to the PC Will I lose everything? Miss my Mac but Vista seems pretty Mac-ish.
Gateway Laptop   Windows Vista  
Gateway Laptop   Windows Vista  

If everything is on the iPod you could copy the songs from there. If you have any iTunes Music Store purchases the transfer of purchased content from the iPod to authorised computers was introduced with iTunes 7. A paragraph on it has been added to this article: Transfer iTunes Store purchases using iPod
The transfer of content from other sources such as songs imported from CD is designed by default to be one way from iTunes to iPod. However there are a number of third party utilities that you can use to retrieve the music files and playlists from your iPod. You'll find that they have varying degrees of functionality and some will transfer movies, videos, photos, podcasts and games as well. Have a look at the web pages and documentation, this is just a small selection of what's available, they are generally quite straightforward. You can also read reviews of some of them here: Wired News - Rescue Your Stranded Tunes
TuneJack Windows Only
iPod2PC Windows Only
iGadget Windows Only
iDump Windows Only
iRepo Windows Only
iPodRip Mac & Windows
YamiPod Mac and Windows Versions
Music Rescue Mac & Windows
iPodCopy Mac and Windows Versions
There is also a manual method of accessing the iPod's hard drive and copying songs back to iTunes on Windows or a Mac. The procedure is a bit involved and won't recover playlists but if you're interested it's available at this link: Two-way Street: Moving Music Off the iPod

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