Transfer Many GB's of Music from Mac OS 10.6.8 to Win 7 PC

I am trying to Transfer 200 GB of Music from my First Gen MacBook Pro to my new Lenovo T430.
I have been sucessful in transfering my newer iTunes Purchases (maybe 400 songs). These are CD based MP3's imported using older versions of
I've tried everything including pretty much ruining a 1 TB Harddrive w/ HFS-now have formatting errors and the vast majority of files fit within the restrictions of universal hdd formats.
All insight & Guides seem antiquated (Most Posted 6-8 yrs ago).
Homesharing worked great in the past but my Mac OS 10.6.8 won't allow this operation nor will my MacBook Pro (A610) allow an upgrade to Lion. The Single Sided DVD Burner is not really fuctional anymore in terms of reliable loading and ejecting w/o CC.
My wife has a brand new MacBook Pro but HIPA/Hospital Policies would frown upon a massive data transfer. My occupation forces me to used the Lenovo and I would like all my music available on iTunes on all my media.
I have searched and tried everything. I am not adverse to paying a token amount but I am in no way buying a 128 gb flash drive.
I have a 400 gb hdd created in Leopard Also not sure what format.
I have at least 800 mb of dupliactes as well, if there was a date exhange service available that took care of the reduncy I would be all the more willing to spend the coin.
Many Thanks!

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