Someone posted that all DRM did was make it difficult for legit users to use their music. I couldn't agree with this more.
The first big realization of how big a rip off DRM is was when I lost about 40 ebooks (that I paid for) when I bought a new PDA. *Some* of this was laziness, but I had ebooks from a half dozen different sources - some allowed a new download some didn't and frankly it wasn't worth my time to go back and figure out where I bought what so I could download a book that I had already read - and none of them would work on the new PDA.
I've since found a place that sells ebooks without DRM, but only along the lines of fantasy / sci-fi (
www.baen.com). I buy all my ebooks there. I do not, except in very rare instances, buy ebooks with DRM anymore.
I do like iTunes, in fact I love it, BUT this problem will eventually come up and bite pretty much every iTunes user out there. One day, you will probably lose most or all of your iTunes library - whether its next year or 20 years from now. You will not be able to recover it by re-downloading, and there is no really good way to archive it. You also cannot sell it, or trade it in for credit a la many used CD / DVD stores. As far as I know, you also cannot insure it like you can a record or CD collection. You can only burn a song so many times to a CD. Basically, iTunes is great as long as you use an iPod, but if anything happens to the iPod line in the future (like, being legislated into oblivion) you could lose the use of literally thousands in music purchases.
Which is why my sympathy is on the side of the pirates and anti-DMCA types, cracking their protection codes. It's through their work that DRM media becomes somewhat practical. If you really want to copy your stuff, you can, even though DMCA makes it illegal to copy your own purchased music from places like iTunes.