Admittedly, a betting man would take a look at Microsoft's recent form and lay this horse straight away.
Item: Tablet PCs are still stuck in a dusty navel located in a small corner at the back of a niche.
Item: The SPOT products such as wristwatches had some doctors worried about the patient's mental health.
Item: The Zune media player even comes in brown casing, the colour of defeatism and the technology equivalent of wearing sweat pants for a first date.
So why, given this miserable run do I think Milan - great football teams but very dull city, by the way - could be a runner?
The answer lies in the positioning. While some recent Microsoft launches appear to have been thrown at the wall, Milan is aimed at a very specific location.
In a Cnet interview, Bill Gates nails his buyer: "That device is in the $5,000 to $10,000 range. You can imagine high-end business environments, even some high-end homes (paying that)."
In other words, the early sell will be to the boardroom and rich idiots, and both of these are beautiful markets.
The rich idiot is the guy - and the rich idiot is almost always male - who wants to show off. He is the buyer of limited edition sports cars, first-class airline tickets and signed football shirts. He is the early adopter needed so that you and I can eventually afford the LCD TV when it reaches the fat belly of the mainstream market. We need this guy but he is a prat, driven by a desperate need to cloak negative self-esteem issues by spending big.
The other category is even sweeter. The boardroom sits at the epicentre of corporate absurdity. The tables cost thousands of pounds and are surrounded by if-it-moves-buy-it, over-engineered technology. This is the lair of huge screens, big projectors, cute cabinets that disguise their contents, top-of-the-range laptops, wireless everything and the motorised soft-eject button. This is the land where the vendors come to restore margins.
Funnily enough, it's rare to find a boardroom where stuff works. Nobody can figure out the coffee-maker apart from the PA, the projector is "on the blink" and the big screen is usually showing the MD's property search page. The table has a big mark on it because, even though it has been custom made and has pop-up monitors, it is not resistant to the scoring and scratching left by hot mugs. The chairs tend to send you through a rapid 360 degree revolution if you move your weight a tad.
It doesn't matter to the buyer though because the boardroom is all about "brand". It needs to be stuffed with the latest gewgaws, no matter how gimcrack, to show that the company in question is "progressive", "go-ahead", "innovative" and the like.
So Milan has a big chance here but Microsoft needs to do a couple of things.
One, it needs to hike the price up to say double or triple the current thinking.
Second, it needs to stop telling people it was originally based on an IKEA table and come up with some fancy brand to attach to it. Preferably German, Italian or Japanese but something reassuring with a logo that has had a lot of advertising moolah invested in it.
And then, Microsoft could have another hit on its hands. µ