Is transfer from Mac to Windows via external HD possible?

I have been using my mums macbook pro and now I'm moving to town for school and only have a HP laptop can I transfer my music over to an external HD from mac to windows and authorise as well? I will visit often and want to have my purchased itunes music on both. If I buy a song on my HP will it update the mac one automatically or do I need to use my external HD every time? And lastly if it does update automatically, what about music not purchased on itunes, will it transfer those as well? I am a mac noob so please keep your answers easy
Thanks any help would be appreciated.

Yes it is possible.
Connect the external drive to the MacBook Pro
Copy the entire iTunes folder from the MacBook Pro to the external drive.
Open the iTunes folder on the external drive
Rename the file iTunes Library as iTunes Library.itl
Delete the files iTunes Music Library.xml and iTunes Library Genius.itdb
Connect the external drive to the HP laptop
Install iTunes if you haven't already, close it if running
Click the icon to start iTunes and immediately press and continue to hold down the shift key until asked to choose or create a library
Click Choose, navigate to the iTunes folder on the external drive and select the file iTunes Library.itl
Authorise the laptop to your iTunes account
If you are based in the US then music purchases made on one machine can be set to automatically download to your other libraries and any iOS devices. The rest of the world, at present, is limited to downloading apps and iBooks purchased from the store. Coming soon is iCloud which will, for a fee, also allow non-store-purchased music to be backed up and synced to your computers or iOS devices via the cloud.
tt2

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