Sync libraries on Mac and PC

Trying to figure out how to sync the libraries on my sisters iMac G5 and her Dell Windows 7. The Mac is running 10.5.8 with iTunes 10 on both. She wants to be able to plug her iPhone 4 to either one without losing the songs. The Mac has her music collection, but the Windows has those few songs that ship with PCs. I can copy the folder from the Mac to the PC, but can I sync them so that as a song is added to one the other syncs up. They bare both on the same wireless netowrk. I had just gotten them to share a printer which went so very smoothly.
I Googled the info, but it hasn't been much help. If I turn on Home Sharing can this prevent the Windows machine from erasing the songs from her iPhone when she plugs it in?

Troubleshooting Home Sharing - http://support.apple.com/kb/TS2972
No way to do it automatically I know of, certainly not with music other than iTunes purchases. The only "automatic" way I know if is to have them share the same library file on a common drive.
Dragging should work. It works in neither direction? Mac iTunes does not support WMA format.

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