My circle of friends have quite a few people who download stuff illegally. However, most just want to try it out / watch it and if they like it they'll pay money for it. The problem with content creation, is your content can suck.
I think my favorite example of someone creating content and essentially letting it be copied (but asking everyone not to) is Louis C.K. [1] He made his stuff easy to download (hell I bought it), priced it reasonably, and asked everyone to please pay.
I actually saw the comedy show first through a friend. I paid him because it was good, and I wanted more content.
In the reverse case, I'm gambling that the content is not only good and worth my time to watch / read / look at, but that it's worth the $X I am being charged. I can see why people don't like this method, and why people download pirated software, movies, TV shows, etc.
Edit: FYI I create a lot of content. Blogs, youtube videos, software. I find the Warren Buffet approach of giving everyone a fair deal, with a terms sheet that's readable works best.
One thing I personally would love to see more of is a full or partial refund policy for every piece of content I buy. I guarantee 99% of people wont use it, but when a movie really sucks or a game doesn't live up to what's promised, you can get your money back. It incentivizes honesty, and it'll help you similar to how it helps stores like LL Bean (where it actually gets more people to buy your product(s)).