> Undoubtedly it is one of the best versions of Windows ever put out

I agree with this. XP was really the first version of Windows that came from the NT/2000 line (rather than the Win95/98 line) that was consumer-friendly. It's hardware requirements were (and are) pretty meager. I know I only upgraded once Windows 7 came out and it became apparent that (unlike Vista) it didn't completely suck.

> at what point does supporting an older operating system like XP cost you more money then it would to spend the money upgrading to a later version of Windows?

Going back to the 90s, it used to be that a new computer was essentially useless within about 3 years, such was the thirst for more power, memory and storage.

But something happened about 5-10 years ago. Ever since then, pretty much any computer you can buy is "enough" for most users, particularly corporate users (which largely comes down to running a browser and MS Office). Microsoft became successful in an era where they could rely on increasing market size and churn to get rid of their old versions. Not so any more.

Some will say "just spend the money and upgrade" but think about it this way: upgrading to Win7 will mean not only buying licenses but in many cases new computers. What if those computers don't actually offer any significant cost savings or improved capabilities for most workers? Think of a hospital that could spend $X million upgrading all their PCs or they could spend that money on an MRI machine or something else which saves lives. In comparison, a computer upgrade can be hard to justify.

One of the reasons I switched to Chrome was for the automatic updates. It's also why I switched all my family members. No one wants to manually run updates. No one even wants the Firefox version of "Install update now?" when you start it (by virtue of you starting Firefox means you want to do something other than wait for it do stuff).

Microsoft needs to integrate the philosophy of continual transparent updates. Unfortunately they're addicted to the revenue of new license sales.

Just recently I looked into buying Photoshop. It's kind of a must-have for digital photography but it's really expensive (for personal use). I discovered that last year Adobe had switched from a license model to a subscription model. Some complained about this. Adobe was famous for doing things like not updating the RAW converter for previous versions of Photoshop to force you to upgrade.

Thing is, their subscription is as little as $10/month. Normally these companies want to recoup the purchase cost in <12 months or something similarly unreasonable. I'm perfectly happy to pay $10/month for Photoshop.

(Some) consumers are willing to pay a service fee of $15/month for TiVo. That's after purchasing the hardware and before paying for any actual content. Why isn't the market just as willing to pay a similar price for something that's meant to protect your private information, credentials photos, identity and financial data?

To me, this is the real power of, say, ChromeOS. Many people only need a Web browser (particularly at work) and don't want to have to spend the time, effort and money to manage their corporate deployment.

And of course MS aren't doing themselves any favours with the clusterfk that is Windows 8...