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cough and Apple is now starting to offer DRM free content because they finally realized its a moot point cough
Because they made a huge amount of money and were able to convince their partners DRM free would now be more money. Including from many of the original sales to upgrade the songs. That last bit of double dipping is both important and unfortunate. But there is no way to get around the fact Itunes was massively successful while totally under DRM, and was only able to build that model under publisher requested DRM agreements.