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Itunes/Back up help!

Hello as a recent new user to itunes I have a few questions!

One is I want to back up my files on my pc and my itunes to a portable media source.The thing is obviously week by week I will have gathered more files so will when im saving new files will it then over write all my old data or will it just add to it?

The thing is im not sure how many times im legally allowed to back up files for say itunes as I obviously want to keep them safe but not break the law!

Also secondly,if for some reason my ipod got lost/broken would I still be able to use my itunes songs that ive downloaded on another ipod device?

Cheers!:beer:
Dec Wins : Gold Leaf Necklace
Jan Wins : Tell No One Dvd

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