The New York Observer has an interesting report on plans the New York Times is formulating to get online readers to pay in some fashion. One scenario involves Times Web content being free until a visitor’s reached a certain word count of number of page views; another would launch a membership system that sounds a lot like a public TV pledge drive. The first sounds unwieldy; the second might work for an august institution like the Times, but won’t save most of the industry.

I cheerfully admit that I’d like to see media companies figure out a way to make consumers comfortable with the idea of forking over cash for digital content. As a reader, I want to see the publications I love prosper, or at least manage to stay in business. As a journalist, I’d like to work in an industry with a business model that ensures that sites like, oh, Technologizer can thrive.

(Note: I have no plans to demand money from folks who read this site. But I just set up a Kindle version of Technologizer using Amazon’s new self-serve blog publishing system–the listing is live, but you won’t be able to subscribe for a day or two. It’ll cost $1.99 a month and I kinda think that I’ll be lucky if I make enough from my cut to buy myself a burrito every now and then.)

I wish I had some profound insight into how the media biz might make readers willing to pay for content again. I don’t. But these points seem self-evident:

1) Once you’ve begun to give something away for free, it’s mighty hard to convince someone that he or she should pay for it;

2) It’s tough to charge when you have direct competitors that don’t;

3) It is possible to charge for usually-free content if it’s in a form that provides new benefits (which is why people will pay for CSI as a DVD box set or an iTunes download even though it’s free on CBS);

4) It is possible to charge for high-quality stuff you can’t otherwise get (which is how HBO became a big business in the 1970s, even though TV had been free for decades);

5) Charging for something new that was never free isn’t inherently implausible (which is why the notion of paying two bucks a month to read blogs on the Kindle makes more sense than blogs announcing that they’re instituting a $2 subscription fee on the Web).

Add up all of the above, and I still don’t see a scenario developing in the immediate future in which millions of people pay meaningful amounts of money for the digital equivalents of newspapers and magazines. Then again, much of the Web’s history to date wasn’t predicted by anyone, so I’m not siding with the folks who say that it’s inevitable that the Web will be (mostly) free forever either.

Let’s end this with a T-Poll:

The P-I will move to a online only source a la the Huffington Post, but it will come at a high cost: the 165-person newsroom would likely shrink to less than 20. In addition, its likely that much of the reporting would be outsourced.

What’s worse, the closure of the P-I, and the earlier shuttering of the Rocky Mountain News, could threaten other papers. Both operated what are called “joint operating agreements,” where competing papers sign agreements to pool operating costs. The Seattle Times and The Denver Post were the other halves of each respective agreement.

Neither were doing well beforehand, and now are faced to pony up for their expenses on their own.

Besides the P-I, other papers are going online. The Christian Science Monitor, which has published in print for 100 years, will go online only in the spring. But some are still trying to stick it out.

The list of papers in trouble includes several high profile names. The Philadelphia Inquirer, The San Francisco Chronicle, The Minneapolis Star-Tribune, The Tribune Company (incudes The Chicago Tribune and The Los Angeles Times), and The Miami Herald, just to name a few.

Most of these are up for sale, but in this economy chances are practically nil that anyone would want to take on a dying industry. So the question remains, is the Web the newspaper industry’s salvation?

Likely not. It still appears that industry executives don’t quite get why newspaper’s initial forays onto the web were not successful. People expect information on the web to be free, and few will pay for it.

This is evidenced by comments recently by newspaper executives at a Pennsylvania University last month.

Houston Chronicle editor Jeff Cohen had this to say about online news:

“When the history is written, 50 years from now, 100 years from now … one of the biggest mistakes the mainstream media made was giving information away for free.”

That kind of thinking is antiquated, and might be proof in the pudding that newspaper execs could be wholly unprepared for the way online news is done if they expect to transfer their businesses online.

It really may be that the super dailies of the 20th Century may become relics of the past, replaced by much more localized papers. You don’t often hear of the local dailies running into trouble as much.

These papers have learned to operate within their means, so they’re likely more prepared to work on a tighter budget.

Either way, the newspaper industry likely has a decade — likely far less than that — to figure out how to survive in the increasingly digital 21st Century. I’m willing to bet we’ll see many more notable papers fall by the wayside before these companies figure it out.

Which is a big deal, since the 82-year-old publisher had as long, influential, and impressive a history of consumer publishing as any company on the planet. Among its titles over the years, other than EGM and PC Mag: Amazing Stories, Car and Driver, Computer Shopper, Creative Computing, MacUser, MacWeek, PC/Computing, PC Week, Popular Electronics, Popular Photography, Stereo Review, Yahoo Internet Life., and many others I’m not thinking of right now. Nobody published more successful mags read by more enthusiasts with a wider range of passions, or made more money doing so.

Ziff Davis remains in business and will be focusing its attention on the PCMag.com Web site network.  Given the state of print publishing and Ziff’s many years of decline as a print powerhouse, its departure from magazine publishing isn’t surprising–and might even be a good idea. It surely won’t be the last old-school magazine publisher that leaves magazines completely behind. But it’s still hard to get my head around the idea that nobody anywhere will read Ziff Davis magazines anymore.

(Necessary but superfluous disclaimer: I spent 18 years working at IDG, Ziff Davis’s principal rival in tech publishing–which is still successfully publishing magazines around the world.)