I think the Humble Bundle is a good measure to how these kind of experiments will succeed of fail. People are now starting to "complain" that they are released too often, and I certainly am seeing less and less enthusiasm for each subsequent bungle but there are still making a shitload of money on them, otherwise they would simply stop doing this.
Personally, I think that in a (utopian) world where media is easily available, not restricted, and is fairly priced (like Louis C.K's video) piracy will still be a major issue. Perhaps it will be reduced but even if content makers manage to compete with the availability of pirated content, they can never compete with the price.
Well there's also the issue of how many games can I play? I've stopped buying from the humble bundles since the combination of that, plus good old games, I have enough games for now. If I had half a dozen unwatched comedy specials on my hard drive, I wouldn't have bought Louis' video.
And, at least for the foreseeable future, there are going to be people for whom it is very difficult to pay for the content rather than pirate it (e.g. kids, teenagers, folks in countries without an online payments infrastructure etc.).
Personally, I think that in a (utopian) world where media is easily available, not restricted, and is fairly priced (like Louis C.K's video) piracy will still be a major issue. Perhaps it will be reduced but even if content makers manage to compete with the availability of pirated content, they can never compete with the price.