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Recently I was looking at Apple's iTunes FAQ documents and the one on "Backing Up Your Music" caught my eye, particularly this paragraph:
if your hard disk becomes damaged or you lose any of the music you've purchased, you'll have to buy any purchased music again to rebuild your library.
I thought that one of the advantages of having a centralized store (like the iTunes Store) which keeps track of your purchases is that you could download it again at any time. A one time download sounds distinctly iffy. As the only supported way of backing up one's music is via DVD or CD -- and there's no incremental support -- anyone with a large collection bought through iTunes is going to have a very, very expensive day when their harddrive finally craters. This is a distinct issue from the DRM one where only authorised computers can play the file: this will affect anyone with any iTunes Plus (i.e. DRM-free) files just as badly.
The upside is that you can manually copy all the files out of the iTunes directory and ensure they're stored elsewhere but for something like this, that should not be required.