Despite the logical nature of Command Line's thesis (he believes that copyright Fair Use is a "right," not just a legal defense) I'm still skeptical about being able to unambiguously explain to people what their "fair use" rights actually are.
At the same time, I don't believe that technology will ever be developed enough to simplify rights and permissions to the point where special dispensations for certain types of uses will become unnecessary. I think there will always be a tug-of-war between those who want copying and usage of intellectual property to be paid for, and those who want intellectual property to be "free."
The other nasty reality is that piracy will always be with us. No matter how well-developed our systems for rights and permissions become, there will always be someone out there ready to game the system.
The way that Command Line discusses Fair Use makes the idea fairly simple: for reasons related to promoting social benefit, at some point in time the rights of the copyright owner are modified and a work passes into the public domain, or there are certain types of uses that are legally permissible without seeking permission. Problems arise since (a) copyright terms (at least in the U.S.) keep getting extended and (b) the actual definition of Fair Use is impossible to codify in an unambiguous and universal fashion.
This situation has been exacerbated with the rise of technologies like photocopying, digital copying, and Internet based publishing. The costs of duplication and distribution keep dropping while the management of the business transactions associated with those rights and permissions keeps getting more, not less, complex (think: DRM).
I'm of the school that unnecessarily complex systems for managing rights and permissions are ultimately self defeating since (a) they cannot operate without error (think: Sony Rootkit) and (b) they have the potential for adding unproductively to the cost of doing business.
That said, I'll be rooting for improved public discussions of "fair use rights," not because I think they will ever be explained and defined in a completely unambiguous way, but because I believe that the natural tendency of many publishers is to attempt to use technology and legal influence to enforce artificial business monopolies. Political support for "fair use rights" is one way to oppose such attempts to control access.
Ultimately, alternative business models that support the more decentralized creation and distribution of intellectual property will evolve. We already see this in a variety of areas, including the use of the Internet to enable independent artists to bypass major music distributors, the use of the Internet to support peer-reviewed scholarly journals that bypass traditional publishing houses, and digital video distribution that bypasses local cable TV companies. (I haven't even mentioned the complex intellectual property issues raised by the increasing popularity of "social media.")
Since it is natural for existing businesses to use all the means at their disposal to protect their interests, including lobbying for additional copyright protection, it is also natural for Fair Use advocates to use public information and political leverage to promote their own interests as well.