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I found iTunes rather easy to work with, although I mostly only use my own music files/CDs, haven't had to deal with purchasing anything yet though.
To get your own music into iTunes, just go to File, Add File (or Folder) to Library and locate where your music is stored on your computer. Warning! If the file size seems big, I recommend converting Selection to AAC (either by right clicking file name in library or by going to the Advanced Tab up top). I didn't do this the first time I tried putting music on my iPod Shuffle, and I could only put 59 songs on it, when I knew it could hold more.
To transfer to your iPod, make sure it is connected to your computer and when you have iTunes open, it should show as an option below Library and Store on the left (mine says's Sonja's Shuffle - the name I gave it the first time I used it). You need to make sure the file you want to transfer has a checkmark in the little box on the left of the file info. Select all the songs you want on the iPod from the library, and literally drag onto the iPod option (below Library and Store). Do not disconnect the iPod during the transfer, and do not shut down iTunes, until it says it is safe to disconnect in the top bubble.
I hope that makes sense to you! Any questions, ask, I might be able to clarify or help.
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