A bunch of print newspapers and magazines seem to be finally jumping on board the iPad subscription train, including The Telegraph (UK), Heart properties including Esquire, Popular Mechanics, and O, The Oprah Magazine, and Time has somehow swung a deal to get existing Time, Fortune, and Sports Illustrated readers free access via iPad.

And, of course, Playboy is coming uncensored (my guess is web app, no iOS-handled subscriptions).

Meanwhile the launched-with-much-todo The Daily has reportedly gotten 800K downloads but is losing $10 million a month.

The big stumbling block was, is, and remains Apple’s insistence that users opt-in to sharing their demographic data with publishers (while the publishers would prefer opt-out since they figure — probably rightly — few users will actively choose to share). Publishers have historically relied on demographics and marketing against them as a key revenue source. Another problem has been getting users to pay for content that they’ve gotten used to getting free on the web — especially when publishers have asked fairly high prices (sometimes higher than print!)

So with more and more heavy hitters hitting the platform, but with everyone still struggling to figure out the business model, what does the future hold for iPad subscriptions? Do we need an iMags/iNews store like iBooks? Or is it just the wrong medium for an outdated message?

What will it take to get you to subscribe?

[FT, WSJ, WSJ, MediaMemo]

MediaMemo is saying Time Inc. is having trouble setting up their own subscription service for a Sports Illustrated iPad magazine app:

Last month, the publisher was set to launch a subscription version of its Sports Illustrated iPad app, where consumers would download the magazines via Apple’s iTunes, but would pay Time Inc. directly. But Apple rejected the app at the last minute, forcing the Time Warner (TWX) unit to sell single copies, using iTunes as a middleman, multiple sources tell me.

First, at the iPhone 3.0 event in 2009, Apple showed off App Store subscriptions for magazines alongside in-app purchase, but while in-app purchases are now fairly common, I’m hard pressed to find a showcase example for App Store subscriptions. What happened to them? Are publishers not eager to embrace them or has Apple not provided the mechanism?

Second, it looks like Time is trying to go around the App Store for subscriptions, kind of like what Amazon and Audible do for users who buy books via Mobile Safari on the web but can then download their library in-app. Is Time trying to do something similar to that but not getting their app approved?

So what happened? The Time Inc. insiders I talked to don’t have a clear answer, presumably because they can’t get one from Apple itself. One theory: Apple is concerned about the publisher’s plans for the consumer data it would collect with each subscription. A darker one: Steve Jobs loves the idea of digital magazines and wants to control the market for himself.

“Darker” certainly scores the melodramatic points, but Apple had no problem rolling out iBooks while still allowing the aforementioned Amazon Kindle app and a host of other competitors. They’ve let streaming music and video apps in to vie for music money against iTunes.

Due to the opaque nature of the App Store approval process, and Apple’s secrecy surrounding unannounced features and technology, there’s never an easy way to tell if a delay is political, business related, or because Steve Jobs will be announcing some new magazine-focused API for subscriptions in September.

These are huge companies, there’s a lot of money on the table, and a critical amount of personal user data behind it. I’m sure we’ll see a lot of foot stomping and fist shaking, and press leaks to spin the story. I’m sure we’ll hear cries that evil Apple is denying big publishers their control, and big publishers are gouging users for digital copies. Fine. At the end of the day I want what I think most end users want — an easy, secure, privacy-protecting way to get my magazines (and comics!) on my iPhone and iPad at a fair price. Apple wins. Publishers win. We win.

Let’s figure that out, shall we?

[MediaMemo, thanks to everyone who sent this in!]

Sports Illustrated has thrown their hat into the ring of media properties racing their content towards a tablet (or mythical iTablet) delivery system for the future. This is part of Time Inc.’s initiative, produced by Wonderfactory.

Apple, of course, has yet to announce an iTablet, but that’s not stopping the declining old-world media companies from getting themselves ready… just in case.

[Thanks to McLaughlin for the tip!]

TiPb just got word from Azuki Systems, the folks behind Sports Illustrated’s SI Swimsuit 2009 [$2.99 - iTunes link] that it’s hit the App Store a tad before schedule.

it’s the first mobile application in the lifestyle category to deliver video of SI’s Swimsuit models, hundreds of SI Swimsuit photos as well as scores, schedules and team information.

The app is rated 17+ since swimsuits and body paint may not be appropriate for every age in every geography, so proceed with all due advanced notice. Additional screenshots, after the break…