I think what he was pointing out is if only apple would open it up so you would not have to pay extra for the privilege to do it.
I do not consider the DRM free songs in the same area as DRM.
Also not all of the iTunes songs can be bought with out DRM.
that's not correct. DRM has been dropped completely. i know there was a transition period in providing all the songs in the store as DRM free, but as i understand, they are now 100% DRM free
here's some additional info on the new business model
http://www.macworld.com/article/138000/2009/01/drm_faq.html
edit:
the $.30 people are referring to also only applies to upgrading your existing library. see article linked above. as for the 3-tier pricing, that doesn't have any baring on whether a track is DRM free or not