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Well, no, that wouldn't work -- since the "five computer" limit is calculated through your .mac or AOL account, you could download a song fifty million times and put it on fifty million computers and only five of them would be able to play it. You need an internet connection to authorize a computer, and the iTunes servers keep track of which computers are authorized via that account. Doesn't matter how many copies of that song you have -- iTunes knows what songs are authorized to play on which computers, and if you try and play a copy of an iTunes AAC file, iTunes servers will still see that you've got that song authorized on other computers.
 
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