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At least as far as the en-US an en-GB versions are concerned for a European like me. I can't check what other countries they work for, so report back if your country/language is not supported.
I find this discouraging:

To install Windows 8 Pro, customers must be running Windows XP SP3, Windows Vista, or Windows 7. If you would like to upgrade from Windows 8 to Windows 8 Pro, click here.

What if I want to install Windows 8 in a VM ? Do I need to install an older version of Windows first ?

You'll need System Builder edition for that.
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After you download the upgrade assistant helper and Windows 8 Pro, there's an option to create a .ISO for a clean install.
Which means you need an older Windows OS installed first, because Upgrade Assistant only runs on Windows, right?
Yup. But what they're selling on their website is only an upgrade version. So it's a pretty reasonable restriction.
Its on sale for $39.99. Just checked the Apple store and Mountain Lion is $19.99. Way to go MS.
This again? OSX versions are more incremental - part way between what MS would call a new OS, or a new Service Pack. MS don't charge anything for Service Packs.

Apple also have lower margins on their OS because it's built into the cost of their hardware.

Justify it any way you want to but MS is getting out competed in almost every area and that is just one more example. Apple gets a small sum every year form their customers and MS pisses theirs off with $140 price tags every 5 years.
I'm guessing you haven't been a sysadmin at any midsize to large corporation...
Apple gets a small sum every year from those of us who bother to upgrade. But every few years they get much more than $140 out of us in the form of the purchase of a much higher-margin computer for which they don't have to split the profits with anybody else.

Also, let's compare apples to apples (ahaha). Apple only retails their OS in an upgrade so we can really only compare upgrade pricing. Apple charges about $20 for an upgrade every year, which averages out to $20/year. Windows 8 upgrades are selling for $40 right now, and the last version of Windows came out about 3 years ago. $40 / 3 = $13.33.

Now I absolutely agree with your assertion that $20 is a fairly small sum. But I'm not sure I agree that $13 is a price gouge by comparison.

(Spoken as a Mac and VMWare Fusion user.)

That works out to ~$28 per year. Just a little more than what an OSX user would pay every year.
Last night people were able to upgrade to Win 8 Pro for $14.99. You could enter ANY information and get the discount code. The deal seems to be dead now that they are asking for legit Win 7 keys. http://www.windowsupgradeoffer.com/en-US
"You must purchase a qualified Windows 7 PC between June 2, 2012 and January 31, 2013 to be eligible for this offer."
Honestly I really don't know what I got out of my $20 from upgrading Lion to Mountain Lion.
A MBP 13" is $1199. Just checked the Dell store and an Inspiron 13z is $699. Way to go Apple.
From what it seems, I cannot download Windows 8 on my Mac for running in Bootcamp or VMWare. I have to download it using an executable from Microsoft that only runs on Windows. This doesn't make sense to me.

Why can't I just buy and download? Why not make it simple and easy for people to access it?

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They're only selling upgrades for the Pro edition on their website for the time being. So if you already have Windows 7 Pro or Ultimate running in Bootcamp or VMWare, that's where you should be running the upgrade executable.

If you're running Windows 7 Home or Home Premium, or don't already have a copy of Windows 7 at all, then what they're selling on their website isn't for you. You'll need to pick it up from a 3rd-party retailer for now. The fine print does suggest that they'll start selling all editions on their website in February. (Maybe they had some sort of agreement with retailers or OEMs?)

In shopping around, I've seen the System Builder edition from a local big box retailer for as little as $80.

Actually the Win8 Pro upgrade is for all edition of Win7.
Yeah, I did the Windows 8 Pro upgrade from Windows 7 Home Premium.
Replying to myself here. Sorry, but it's obviously not clear. I don't know if Microsoft wants to hide this or they are assuming everyone has a copy of Windows already or what.

Anyway, I just ran through this process at work. I downloaded the executable. Purchased Windows 8 for the price shown, $39.99.

It took me through some steps. At the end, it gave me the option to create an ISO. I have done this and will try it later tonight when I get home to see if it lets me do a clean install of Windows 8 on VMWare.

I'm afraid you're going to be disappointed. The Terms and Conditions make it clear this is only for upgrading a machine that already has Windows installed on it:

"Each upgrade license applies to only one PC and you can install the upgrade only on PCs that have a valid base license and one of the following operating systems: Windows 7, Windows Vista, or Windows XP (SP3)."

http://windows.microsoft.com/en-US/windows-8/terms-condition...

During the upgrade process, you have the option of reformatting the hard drive and doing a "clean install", but it must be on the same disk that already has Windows installed on it.

http://answers.microsoft.com/en-us/windows/forum/windows_8-w...

Yeah, I screwed up.

Then my co-worker got me to mount my ISO in VMWare, run the installer in Windows 8. It asked for the key. I put it in. It activated... I think. Successfully. I used it all weekend so far, without any issues, except I can't figure out how to use it, haha.

Keep in mind that this is essentially an "upgrade" version. You can't do a clean install with this version. You'll pay $40 only to upgrade it from Windows 7.
Yep, was able to buy upgrade version from evaluation version of Windows 7.
I only use Windows to play games on steam. Would it make sense for me to upgrade?