Anyone contemplating a business that depends on using DRM to control their customers ought to read Cory Doctorow's story at BoingBoing. Cory says:

So, the "FairPlay" system [Apple's DRM system] was punishing me for:

1. Buying so much iTMS music that burning it to CD and ripping it back as MP3 (and re-entering all the metadata) was too big a chore to contemplate
2. Buying a new Powerbook at full retail every 10 months
3. Buying new Powerbooks as soon as they are announced, before all the manufacturing bugs have been shaken out

Apple tells us that its DRM "keeps honest users honest." I'm a pretty honest user. Apple's DRM hasn't kept me honest, though: it's kept me angry with Apple. It's kept me feeling like a sucker for giving them my money. It's kept me in chains.

From Boing Boing: VLC will play iTunes Music Store tracks
Referenced Fri Mar 26 2004 11:05:59 GMT-0700

This frames Apple's dilemma perfectly: can it afford to punish the buyers of $3000 computers to protect $50 worth of content? It doesn't take an MBA to see the problem with this strategy. Business Week has a different tack for Apple: license Fairplay to other music vendors and get out of the music store business. That might keep people who buy Apple's gear from being mad at Apple, but it still doesn't solve the real problem for online music: DRM alienates the people who pay your salary: your customers.