Pushing music/content that randomly stops working when the providers shuts off their drm servers (hello Yahoo, MS), or the provider in a Big Brother moment decides you can't have the file (hello Amazon), or you hose your OS and reinstall, etc, is a very user-hostile thing to do... Inexperienced users might get burned by DRM once and lose their files, after that they'll surely stick to piracy...
Not that I condone it, but when the choice is between paying for broken stuff that doesn't work, and not paying for stuff that works, something is wrong...