Dobey, you have some interesting remarks. However, in the end, you are wrong. You are saying that not DRM, but iTunes (or insert some other term here) prevents me from using my music the way I want it to. This is blatantly false.
A gun is meant to shoot people. Not to be used as a teddybear replacement, try it, your son will shoot himself eventually. Similarly, DRM can be argued to not be restrictive, but that is purely theoretical. For all practical purposes, mostly due to political blabla such as laws preventing circumvention and explicit denials to remove DRM from said music, DRM is restrictive. I cannot copy my iTunes-purchased Britney Spears song to my mp3 player because of DRM and its politics. This is not just a flaw in iTunes, but a flaw in the business model. A serious flaw which makes us worry about DRM and its surrounding politics.
And now don’t say that it is not because of DRM, because without those politics, DRM would not be pressed upon us by the industry and would thus not exist.