Here’s a BusinessWeek article about how “Microsoft is Fighting Back (Finally)”.  The most interesting part is about Microsoft’s new “Windows Anytime Upgrade” strategy. Here are some details:

“Because of the smaller size of Windows 7, three versions of the program will come loaded even on lower-end machines. If a consumer on a cheaper PC running the “Standard” version tries to use a high-definition monitor or run more than three software programs at once, he’ll discover that neither is possible. Then he’ll be prompted to upgrade to the pricier “Home Premium” or “Ultimate” version.

Microsoft says the process will be simple. Customers enter their credit-card information, then a 25-character code, make a few keystrokes, then reboot. Brooks says pricing hasn’t been determined, but upgrading “will cost less than a night out for four at a pizza restaurant.””

After reading this, I instantly thought about Cote excellent post titled “The Return of Paying for Software” from last summer.  Cote wrote:

“When it comes to making money with software, the iPhone App Store is the glossiest example of trend I feel creeping up on us: people paying for software.

Yes, people have been paying for software forever, but the expectations for most consumer software of late has been that it’s free.

…

The change here is an environment where people will spend $0.99 to $20 for a piece of software. I often comment that this user-mentality – spending small amounts of cash on software – exists in the OS X world, but it’s been lacking from others.”

While I initially balked at the thought of a popup window with: “Hey, it looks like you can afford a high definition monitor, so why not get the most out of it with Windows 7 Home Premium, for an low price of $19.99?”, I’m willing to give this idea the benefit of the doubt.  This recent NYT article (via Cote – that man is Gold!) explains the success of an iPod/iPhone game called iShoot, and is a reason behind my openness to the Windows Anytime Upgrade strategy:

“In January, he released a free version of the game with fewer features, hoping to spark sales of the paid version. It worked: iShoot Lite has been downloaded more than 2 million times, and many people have upgraded to the paid version, which now costs $2.99. On its peak day — Jan. 11 — iShoot sold nearly 17,000 copies, which meant a $35,000 day’s take for Mr. Nicholas.”

Consumers are getting accustomed to acquiring software for instantaneous incremental gratification.  The consumer gets some value off the bat, but is faced with a purchase decision to get incremental value.  When the consumer decides to follow through with the transaction, the gratification is instantaneous, not tomorrow in the mail or through a 4hr download.  With the Windows Anytime Upgrade strategy, consumers would get some value off the bat.  Upon hitting a feature/function wall, a purchase decision would be presented.  And if the consumer chooses to transact with Microsoft, it seems that the incremental value would be provided on the spot, without having to download or acquire and install another DVD’s worth of an OS.

Seems like an interesting strategy that’s much closer aligned to how consumers pay for software today.  Maybe an unexpected outcome of Apple’s App Store strategy is to educate consumers ahead of Microsoft’s Anytime Upgrade strategy.