If you actually want to use music you've purchased from iTunes

This post is "old news", but describes a problem I have only recently encountered. I have mixed feelings about digital copyright as a law-abiding citizen. Sure, p2p filesharing - sharing digital music files purchased once and then copied millions of times across the internet - doesn't sit too well with me ethically. But, the restrictions iTunes places on music legally purchased for personal use are way too onerous. For example, the 5 computer limit on sharing the files, the fact I can't transfer files I've bought to my wife's iPod, the limit on burns to CD, or the fact I have to use iTunes to play all of the files I've bought.

In Apple's Defense
Understandably, when Apple established these rules and regulations, they were probably reacting to the possible legal disaster that its cash cow is going to somehow be sued out of business by whining rockstars with expensive lawyers. Certainly, the fact iTunes came out in the wake of Napster and P2P file sharing hysteria was probably a contributing factor in iTunes onerous DRM requirements embedded in each AAC file consumers buy from iTunes.

With that said
With that said, the DRM (digital rights management) imposed by Apple renders music I've legally purchased strips away functionality of these files for my own personal use. I can't put our prenuptually-purchased songs on my wife's iPod. I can't take the files, convert them to MP3s to submit as part of my own podcast on iTunes.
Sure, emerging technologies were first feared by authors, musicians, and Hollywood. The photocopy machine was seen as the death of publishing for authors. Yet, the average American has never photocopied an entire book and sold it on the black market, or prevented an author from getting royalties by giving it to a friend. Dual-tape decks and two VCRs were also seen as the end of music and movies respectively, but the poor quality of copies was an obstacle. Obviously, digital files like .mp3, AAC, and even the CD do not decline in fidelity when copied, which is a very real fear for artists. But, as much as I support the desire of the music industry and Apple to prevent mass piracy (good luck, especially in China), I have a right to be able to use copies of music I have purchased for my own personal use. I also have a right to play AAC files using whatever player I chose, especially if I hate the iTunes interface.

hymn Project
The hymn (Hear Your Music Anywhere) project shares this philosophy. The java-based program strips AAC files you've purchased and allows you to use them in a player other than iTunes, to re-encode them as MP3s if you decide that you hate your iPod (God only knows why), and to otherwise use them as you, the legal purchaser, should be able to do. I have had a lot of success with the program, but be sure to read the instructions carefully before you use it.