People are surprised that the New York Times paywall is working out pretty well, and I would count myself among them. For my part, I never thought that the principle of a paywall was crazy, only that the particular model the Times had chosen seemed excessively complicated. Regardless, I'm wondering if we should really be so surprised that people would be willing to pay for a website.
It's been conventional wisdom that people simply wouldn't pay for electronic content for some time, but I think there were two related but separate issues clouding our judgment: a) the lowered cost of distribution's inevitable downward pressure on prices, and b) the fact that the Internet used to suck.
A) is pretty simple. When you get to the point where it's essentially free to distribute something, customers are naturally going to put a lot of downward pressure on prices. Small and large publishers alike are freaked out by the demand for ebooks at nine, seven, and five dollars, or even one dollar, but the idea that you can charge hardback prices (and pay your authors hardback royalties) when you've cut your overhead to the bone is ridiculous. Consumers know better, but it wasn't until iTunes that we started to see digital content priced in a reasonable way by any retailers with juice. Now with online content retailers like Amazon, eMusic, Netflix, and etc. beginning to charge prices the market will bear, it certainly seems to me that people are paying quite a lot for digital content.
B) is something that becomes painfully clear in retrospect. Back when people started selling content online, the Internet sucked. Their websites were hideous and barely usable. Broadband was rare enough and bandwidth cost enough that if you wanted to pay for something big, it was legitimately best for everyone involved to just order the CD, at which point you might as well go to Wal-Mart or Best Buy or whatever and skip the shipping. Major corporate websites like that of the New York Times were usually ahead of the curve, but not by that much -- and in all honesty, that site still kind of sucks (I might subscribe simply for the ability to turn off the "too many stray clicks and we'll load up a dictionary page" feature). The Internet is almost good these days! It's often very close to user-friendly! And as we feel more confident in retailers, we'll probably make more digital purchases, and more often. That's certainly been my experience.
Which makes sense: people are offering services I want at prices that seem reasonable in forms I can easily use. That's, uh, how you make a sale. The Internet may make it more difficult to create and market mega-hits, and the fragmentation of markets may even reduce full-time professional participation of content creators generally. But the idea that people will simply refuse to pay for things they value strikes me as unrealistic. Yes, we can often just go bittorrent it. But honestly, bittorrent is a bit of a hassle, and I like giving my money to the people who do things I care about.