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.