The Digital Skeptic: Why Does Everyone Hate Windows 8?

NEW YORK ( MainStreet) -- When you're dealing with Microsoft ( MSFT) it's not that it's going to get bad, it's about managing how bad it's going to get. Take its radical new touch-based desktop and tablet operating system, Windows 8, due out this year.

Never mind investor grumbling about the ugliest rollout of any major tech product, probably ever. Company management is pretty much winking at the ugly days ahead.
Microsoft's radical new touch-based desktop and tablet operating system, Windows 8, is due out this year.

"Designing a new release of a product already used by a billion people in a billion different ways is, as we say, like ordering pizza for a billion people," said Steven Sinofsky, president of Windows, in a company blog post.

And at least based on my months of testing and considering the medium-term exposure, I can confirm Steve is correct. Windows 8 has a long, strange road ahead.

Here's what investors can plan on.

A surly countdown to 8
Keep in mind that the Windows 8 liftoff has in fact already begun. Last week Microsoft formally rolled out a "release preview" of the product, probably the final riff before the full code is released -- I am guessing sometime in October.

Don't bother downloading and/or installing it. Much more interesting for markets, anyway, is the roughly 11,000-word (honestly it might be longer) blog post by Jensen Harris, director of program management for the company, called "Creating the Windows 8 user experience."

Here the beastly truth of what investors are facing is clear: This company is utterly and totally invested in the principles behind Windows 8, no matter what anybody thinks. No traditional "Windows" layout, a focus on touch-controlled technology and the ability to work for PCs, tablets and other devices. That means there will be no backing down from this offering. And no New Coke, Microsoft Kin, here-today, gone-tomorrow investor bailout if things go south.

In short, Redmond is committed to 8. It's do or die with this product. Yikes!

Bet on some major 8 "Hate"
Between Microsoft's well-established negative brand equity -- to me, only General Motors ( GM) is worse -- and the software maker's third-grade marketing acumen, investors can bank on viciously negative buzz for Windows 8, a drumbeat of crankiness that will only build until the fall launch.

At which point, things will turn really foul.

Remember, it won't be just PC users bitching and moaning about being forced to learn a new way to use their computers. This product is also deploying on mobile tablets and, in a sense, smartphones, because Windows 8 is really the PC version of Windows Phone. So the drumbeat of complaints will pour from everywhere well after the official launch.

No Windows holiday cheer
Worse -- oh yeah, it gets worse -- the Windows 8 rollout will be compounded by the holiday timing of the launch. A la Marooned, that Gregory Peck sci-fi potboiler where a rocket launches in the eye of a hurricane, Windows 8 will attempt to lift off in the teeth of the holiday hype season. A season, mind you, with not just one, but two products that will crush Windows 8: whatever Apple ( AAPL) product is new to market, say the iPhone 5. And Amazon's ( AMZN) Kindle Fire tablet. Both have their own software. And both will be seen as a better alternative to Microsoft.

That means if you are in any way tied up with Microsoft -- stock, bond, derivative, whatever -- bet on at least a few bad patches sometime in the next quarter or two with this company.

It simply has to happen.

The PC strategy works -- eventually
What stabilizes the situation -- and keeps investors from sending this company to its doom -- is that Microsoft will not drop dead over Windows 8. Remember, it's not really a consumer products company; it's a software provider for PC makers. And this PC-based armada of Dell ( DELL) and HP ( HPQ) and Toshiba and Lenovo, have just about had enough of getting its head handed to it by rival Apple. Traditional PC makers, therefore, will have little no choice but to force Microsoft's new OS into markets.

And slowly -- like maybe Q2 of 2013 -- Windows 8 will eventually find its footing in the marketplace. And dollars will flow back to the company bottom line. And into investors' pockets.

All we can pray for is that by the time Windows 9 rolls around, that can done with a lot less trauma.
This commentary comes from an independent investor or market observer as part of TheStreet guest contributor program. The views expressed are those of the author and do not necessarily represent the views of TheStreet or its management.