Great speech. I think I can answer about 50% of your questions though, thanks to the daily copyright issues people have to solve over on Wikipedia.

However, I got two simple answers to the whole posting:
1) Go the way of filesharing. Not by being large at copyright infringement, but exactly by pushing the limits to *see* the limit. If people all around the world are breaking copyright law because in their mind it's fair use, then *that* should define copyright, so hopefully something will change.
2) Go Creative Commons. If you find the idea that you can't publish a photo of a 1970s band or something because the copyright lasts till after the 2100s, then maybe you want to change this fact for people who want to use your content: Go with an easy-to-use free license from the Creative Commons.

Sounds interesting... what is your involvement at Wikipedia?

As for pushing the limits, well, but when a company sends me a cease-and-desist, I don't think I have the ressources to get into a fight – even when I would think it's "moral", I wouldn't know if it's perfectly legal...

About Wikipedia: I'm just a regular registered contributor, don't even contribute much. But after reading many of the heated discussions about copyright (flags, images, text) and their conclusions you start to get an idea about the answers to some questions.

For derivative works, the amount of creativity involved is often important: A photo showing just a painted (copyrighted) picture is infringement; A photo showing a gallery of copyrighted pictures in the article about a gallery might not be infringement, because it's used to illustrate something else. Of course the creativity involved will have to be checked by a court, so it's not really a win.

Did you know that nowadays it's copyright infringement to photograph the Eiffel tower at night? It sounds stupid, but the company maintaining the tower applied a copyrighted light pattern, and so now it's probably illegal to make photos at night. This is something that's still in heavy discussion in the WP though.

About pushing the limits: I think I have to rewrite that part from above.
Sure, if you get into a legal fight, there's no way you can win. The company fighting for "their right" will just throw money at their lawyers, and they'll drag you from court to court and you lose a hell of a lot of time and money. You might get the money back at the end, but that's nothing against the stress involved.

So the way to act *could* be like the file sharers do. Why is file sharing doing so well although the content industries are suing the hell out of people? Partly because people calculate their chances of being sued and don't deem it possible. If in a network of 4 million people 1.000 are getting sued for copyright infringement, that's less than 1%, it's 1 out of 4.000 people. If you take all file sharing networks together it's even less.

My advice is not to go downright illegal in media usage. It's rather: If it's a good part of the law or a bad part of the law: Agree to it. This means if somebody has to be dead 70 years before you can use his photos, then it should be that way. But if a part of the law is totally ridiculous (like the fact you can make photos of the Eiffel tower illegal because you applied a copyrighted movie poster or something to it), then ignore it.

The line between good/bad and ridiculous should be drawn by the people of a community, so their view of copyright has more weight. If bloggers want to post a copyrighted picture of some 1950s band (>50 years old, not >70 years old), then they should do it! This is probably the only way to change this rotting copyright system.

Another word about communities: I'm pretty sure that a change in copyright law, which just has to happen within the next years, will come from open content people, hopefully including projects like the Wikipedia. Because when you run a website that is currently on the 71st place of most-visited websites (Alexa), people *will* listen to you.

So, the ideas are: Be moral, and *hope* you won't get sued. If enough people step over the line, something will change. And join forces with powerful people who are on your side: The Creative Commons and Wikipedia people, as an example.

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P.S.: This doesn't even have to do with copyright anymore, but I just wanted to mention that you don't have to do something wrong to be sued into oblivion anymore. A Wikipedia admin had a private forum somewhere (not WP-related). A lawyer sent him a letter telling him it was illegal that somebody posting on the forum was linking to a site that linked to a software making copy-protection circumvention possible (2 level link!). They wanted the lawyer's cost of course. He was totally on the right side, because by the logic of this lawyer, Google would be highly illegal. But the small guy couldn't fight for his right because he didn't have the money.
The bottom line: You don't need copyright infringement on your blog to get sued; You can get sued anytime for anything, and you won't be able to fight back even if you're right. As I said before: Something *has* to change here.

Hehe... didn't really expect to get on the front page, although my posting was rather lengthy. ;)

Anyway, I want to back up some of my words now.

http://www.tour-eiffel.fr/teiffel/uk/pratique/faq/
The FAQ of the Eiffel tower, saying that you can't take pictures at night. I can't find the discussion on the Wikipedia... I guess it was mostly IRC and the mailing list where this happened. It's true though, as the FAQ states.

http://de.wikipedia.org/wiki/Wikipedia_Diskussion:Bildrechte
This is the (German) place for all image copyright talks. Lots of interesting discussions going on. Unfortunately there are no copyright lawyers involved, but of course some Wikipedians have become rather good copyright advocates themselves over the Wikipedia work.

Found the discussion on WP now...

http://commons.wikimedia.org/w/index.php?title=Commons:Deletion_requests&oldid=94361

A quote in there says they won't go after people publishing photos of the Eiffel tower at night for free. They are only worried about commercial use. However, what happens when your free blog with the pics gets #1 for Eiffel Tower on Google? Also, this "we won't go after you" is not at all compatible to the GNU FDL (Wikipedia's license), because it's not legally binding (and the GFDL *permits* commercial use).