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Hey, I here ya . I'm a Mac user as well.
I'm not sure you'll get Windows as cheap as you want it, but they really could just make one freaking edition and that's it. The only reason Apple can offer OS X as cheap as they do is because they make money off of Mac sales. Microsoft doesn't make much money off of individual PC sales, so they compensate. Plus, people will buy it, and they know that. Vendor lock-in plays a part in this. To Apple, your additional OS X purchases are regarded as upgrades. Even though they can be installed cleanly, the idea is that you bought that disk to upgrade from a previous version of OS X. You've already got an OS X license, which you paid for at the same time as your Mac--a package deal, if you will. It's a different mentality. Also, they're trying to make their os more attractive to both individuals and enterprises at the moment.
And how long do you think it would be, if OS X were to ever run on standard PCs officially, before an activation scheme would be introduced? At the moment, Apple really doesn't have to worry about it, but they'd implement something in a heartbeat if piracy of OS X became as rampant as it is with Windows.
Don't get me wrong, I love OS X and the Mac platform. I'm glad OS X is so cheap compared to Windows, and I'm glad there's no activation. Just trying to point out why this is the case, and that it is like comparing Apples and oranges (yes, pun intended).

Speaking of cost, there's price, and then there's release cycle.

You pay for XP (2001) and for Vista (2007). ==> 2x

Meanwhile, you pay for Cheetah(/Puma) (2001), Jaguar (2002), Panther (2003), Tiger (2005) and Leopard (2007). ==> 5x

However, both OSs come installed, and most non-techie Mac/Windows users that I know (ie. rep. of majority of market), never bother upgrading their OS, until they buy their next machine.

The point above, to some extent, deals with the issue of customer confusion as well. Also, I believe only three editions of Vista are available off the shelf, not that hard to choose from, and still upgradeable at any time.

Of course a single version is preferred, but Microsoft is marketing it's product to a much larger base, so they can make a few more bucks by having different price ranges.

Edited 2008-12-23 00:05 UTC

Better than paying £300, once, for a turd in a box.

Actually most people Didn't pay for Vista

Yup, me too, but I'm running Linux distros (flavors change frequently). A few bucks and I'm in business. Microsoft needs to change it's business model (commonly known as greed).
When I find a distro that perfectly fits my needs, I'm happy to pay the developer a reasonable price for his work. I resent being screwed (forced to pay through the nose) by some company (unnamed, but you know who I'm talking about) out of high dollars for a piece of crap! Then, I resent having to beg for an activation code every time I change a piece of hardware which is very frequently. This is a big irritation to me.
Thus, Linux.
But, I do hope that Windows 7 turns out to be a quality piece of work so that those who don't like steep learning curves (like Unix geeks) will finally get what they pay for.