As far as First Purchase doctrine and software goes, I believe the courts generally rule in favor of the consumer as the 'license concept' that the software industry practices is actually in violation of several portions of the Clayton act (I'm all new to this so I could be wrong in my understanding), where basically that license has to be agreed to "post purchase", ie: AFTER you've given your money for the software, you're then presented with the EULA. If the EULA was made available AT THE TIME OF PURCHASE then it would work more towards, "No they're not buying a copy, they're purchasing a license..." argument. Also, considering that we purchase software with the understanding that the package we've purchased is ours for as long as we want it, ie: there's no expectation to return it to the software company it came from at any time, again, it makes the software a purchased item, not a licensed item.
Now when it comes to the question of DRM'd works like eBooks, movies, and songs and such. I think the only legal question would be is can you break the DRM, and sell/rent/trade/give away a non-DRM'd version even if you've destroyed/deleted the original DRM version.
I understand that legally you do whatever the heck you want with the copy of the work you purchased for your own use as long as it doesn't some how violate copy right law (like maybe taking a book and painting the entire text on the exterior of your house such that anyone walking by could read the book, an extreme example but I think you'll get it). So I think the sticking point will be, when you sell/rent/trade/give away a purchased work it had better be as damn near possible to original purchase condition (excepting standard wear and tear) as possible otherwise you may have legal issue.
This is why this is actually so different from software/music/movies that we purchase. If the function of the DRM embedded in the package you purchased said work makes it impossible to transfer unaltered, well, tough crap. That's what you purchased. There is a potential with DRM on print items to make the work unreadable other than on the device the work was originally purchased to work with.
Due to how software/music/movie CD and DVD's and their respective players are constructed, it's not really feasable to alter the media/content after the fact so that it only plays in the player it was originally used in. I can buy a DVD that was rented to 50 different people and it will still play in my DVD player, unaltered. With a DRM'd book, that's not always possible without altering the file you purchased.
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