Over the course of this OS comparison, I fully expect Windows 7 and Mac OS X Snow Leopard to be pretty comparable, from a functionality perspective. Sure, there will be solid wins here and there for each system. But what I didn't expect was for either system to just out-and-out dominate the other, and laughably so, in any given category.

Well, prepare for a chuckle ... if you're a Mac user, that is. Windows users, by contrast, have a lot of work ahead of them, and a lot of complaining to do. The issue is that Windows 7 pricing is as convoluted, ridiculous, and hard to understand as it was with Vista, and I'm reasonably sure no one would ever hold up that product's pricing and licensing as a model of clarity. If you're looking for a real-world beat-down of Windows at the hands of the Mac, there is no better example than pricing.

It wasn't always this way. In fact, Apple regularly charges its Mac OS X-using customers an exorbitant $129 per release, and it did so over the past four versions. (10.1 was the sole free update.) If you include the original version of Mac OS X in the equation, your typical faithful Mac user could have easily spent about $650 on OS upgrades since 2001, per Mac.


What's interesting about this is that Apple, at one time, was making fun of Microsoft for not releasing an OS update between 2001 (Windows XP) and 2006 (Windows Vista). The truth is, Microsoft released numerous OS updates, including Windows XP Service Pack 2 (SP2), two versions of Windows XP Tablet PC Edition, and four versions of Windows XP Media Center Edition. Microsoft didn't charge customers for any of these updates per se; you simply got them with new PCs, which is how Windows users almost universally acquire their OS. (Apple, by contrast, gets a big retail boost from upgrades each time they ship an OS X update.) So while some Mac users were spending several hundred dollars per Mac for OS updates between 2001 and 2006, Windows users spent ... well, nothing. The mind boggles thinking how Apple would have marketed Windows XP SP2.

But none of that really matters now, does it? Because what we're looking at is the pricing for Windows 7 and Mac OS X Leopard. Let's take the Mac first, since it's so easy.

Mac OS X Snow Leopard pricing

If you are a Mac user running the latest version of Mac OS X (Leopard)--and by the way, that is most Mac users--you can upgrade to Snow Leopard for just $29. You could also opt to get the five-Mac Family Pack for just $49. If you have the next-oldest version of Mac OS X (Tiger), which dates back to 2005, and are running a modern, Intel-based Mac, you must instead get the Mac Box Set for $169. This set includes Mac OS X Snow Leopard, iLife '09 and iWork '09. (A five-machine Family Pack is also available for $229.)

And ... that's about it. There are no real gotchas beyond the fact that Mac OS X Snow Leopard has been engineered to work only with Intel-based Macs, or, put another way, modern Macs. So if you are still using an old-fashioned PowerPC-based Mac, Leopard is the end of the road for that machine. (One might be tempted to debate the pros and cons of Apple's speedy technology obsolescence mantra, but let's be serious. Most Mac users, again, are on new hardware already. That's what this market is all about.)

Oh, and did I mention that there is only one "version" of Mac OS X Snow Leopard? Get this, it's called Mac OS X Snow Leopard. It includes all of the features that Apple designed for Mac OS X Snow Leopard, and not some weird, arbitrary subset of Mac OS X Snow Leopard features. There's no Mac OS X Snow Leopard Starter, Mac OS X Snow Leopard Home Premium, Mac OS X Snow Leopard Professional, Mac OS X Snow Leopard Enterprise, or Mac OS X Snow Leopard Ultimate. There are no weird "E" editions for Europe, "K" editions for South Korea, and no Home Basic version for developing nations, whatever that means. You can't only buy Mac OS X Snow Leopard on low-end Mac hardware, or on high-end Mac hardware. You just buy a Mac and get Mac OS X Snow Leopard. What a concept.

[ For more information, read my overview of Mac OS X Snow Leopard. ]

Put simply, Apple's best customers are finally being rewarded with extremely low pricing on Snow Leopard. Yes, they may have paid more over the years. But there is little doubt that Snow Leopard pricing is simple, clear, and inexpensive. It just is. To claim otherwise ... It just boggles the mind.

Windows 7 pricing

Speaking of "boggling the mind," let's take a painful stroll down the Windows 7 pricing and licensing path. It's like the Bataan Death Match ... but this time, the victims are your sanity and your wallet. I'll try to make this as brief as possible, starting with the high-volume Windows acquisition schemes and moving down the list.

With a new PC

The vast majority of individuals who run Windows acquire it with a new PC. With Windows 7, there are four possible versions that you can get, each with a different cost, and which choices you receive depend on the type of machine you're buying and where you buy it. (Actually, there's a fifth choice, Windows 7 Home Basic, if you live in a developing nation. Let's just pretend that doesn't exist for a moment for simplicity's sake.) These choices, from least expensive to most expensive, are:

Windows 7 Starter. Available only on machines that meet Microsoft's restrictive netbook definition (i.e. single-core Atom processor, 160 GB hard drive or smaller, 10.1-inch screen or smaller), Windows 7 Starter is the least expensive Windows 7 version. It's also the least useful, and lacks basic niceties as Aero glass and even the ability to change the desktop wallpaper. Yes, seriously.

[ Read more about the limitations of Windows 7 Starter. ]

Windows 7 Home Premium. The volume version of Windows 7 for individuals supplies the vast majority of features we associate with Windows 7. And unless you need domain support, it's the obvious choice for virtually all mainstream Windows users. However, it costs a lot more than Windows 7 Starter, so adding it to a low-end PC will demonstrably change the price of that machine. That said, it is the most commonly offered Windows 7 version with new PCs.

Windows 7 Professional. The mainstream Windows 7 version for small businesses, Windows 7 Professional provides domain access and only costs a bit more than Windows 7 Home Premium. Major PC makers offer this version on business-class PCs.

Windows 7 Ultimate. The most expensive Windows 7 version, Windows 7 Ultimate includes every single Windows 7 feature. Because of its prohibitive pricing, this version will be less commonly offered by PC makers. Expect to see it more often on high-end PCs, especially gaming PCs.

Retail and electronic download

With Windows 7, Microsoft and its retail partners are again offering the three mainstream Windows 7 product editions--Home Premium, Business, and Ultimate--in retail packaging, but sadly each edition ships in two versions:

Full. This is the more expensive version. It provides clean and upgrade/custom install capabilities and is aimed at those users who wish to install Windows 7 on a PC they built themselves that didn't come with a previous version of Windows.

Upgrade. The less expensive version, Upgrade packaging provides for clean installs, in-place upgrades (from Vista only), and migrations (Vista or XP). The licensing is more restrictive than that of Full, as the PC to which you're installing this product must have come with any version of Windows XP or Vista.

New to Windows 7 is the availability of an electronic download of the Windows 7 Setup media from the online Microsoft Store. As with the retail packaging, both Full and Upgrade versions of Windows 7 Home Premium, Professional, and Ultimate are available. Unfortunately, you don't save any money by buying Windows 7 electronically, which seems silly.

Also new to Windows 7 is a (temporary) package called the Windows 7 Family Pack, which provides three licenses for Windows 7 Home Premium Upgrade. It's only available in retail packaging (i.e. is not a downloadable option) and is not available for users who want Windows 7 Professional or Ultimate instead.

Also new to Windows 7 is that all retail versions come with both 32-bit and 64-bit Setup discs. With Windows Vista, only Ultimate edition included both discs. If you buy an electronic version of Windows 7, you must choose which one to download at the time of purchase.

Here's how the Windows 7 retail/electronic download pricing breaks down (in the US).

Windows 7 Home Premium (Upgrade) $119.99
Windows 7 Home Premium (Full) $199.99
Windows 7 Family Pack (Upgrade, retail only) $149.99
Windows 7 Professional (Upgrade) $199.99
Windows 7 Professional (Full) $299.99
Windows 7 Ultimate (Upgrade) $219.99
Windows 7 Ultimate (Full) $319.99
Windows Anytime Upgrade

[ Read more about Windows 7 pricing. ]

Because of the sheer number of Windows 7 product editions, Microsoft also offers an electronic version upgrade that lets you pay a fee (naturally) and upgrade whatever version of Windows 7 you're using to a higher-end Windows 7 version. How convenient. Actually, it works really well--Windows Anytime Upgrade runs for about 10 minutes and then you're good to go--and no disc is required.

Windows Anytime Upgrade pricing breaks down like this:

Windows 7 Starter to Home Premium $79.99
Windows 7 Starter to Professional $114.99
Windows 7 Starter to Ultimate $164.99
Windows 7 Home Premium to Professional $89.99
Windows 7 Home Premium to Ultimate $139.99
Windows 7 Professional to Ultimate $129.99

[ Discover Windows 7's Windows Anytime Upgrade capabilities. ]

Student pricing

Microsoft also offers a special college student-only deal for $30: You must have an .edu email account and choose between Windows 7 Home Premium Upgrade and Windows 7 Professional Upgrade. Annoyingly, it's download-only, and doesn't come in a standard ISO format that you can easily burn to disc. (On the other hand, Apple doesn't offer an education discount for Snow Leopard.)

Final thoughts

Score one for Apple on this one. Most Mac users will pay $29 to upgrade to Snow Leopard, while a smaller customer group will pay $169. Those interested in a multi-Mac license can get a Family Pack. In any of these cases, install and upgrade is straightforward, and while one might argue that Snow Leopard is a less compelling upgrade than Windows 7--we'll get to that, believe me--no one can deny that Apple makes the upgrade process easier and a heck of a lot less expensive.

On the Windows side, wow. It's a mess. You'll pay anywhere from $30 or so for the privilege of getting a very low-end Windows 7 version on an underpowered netbook to $320 for the Full Meal Deal. Most will pay somewhere between those two numbers, but it's like spinning a roulette wheel. We have no real understanding of what Windows 7 costs when bundled with a new PC per se, but we can look at the convoluted retail pricing structure for clues. It doesn't help that Windows 7 comes in four versions for individuals, in both Upgrade and Full packaging, with different 32-bit and 64-bit installers, and with various in-product upgrade paths. Further confusing matters is the upgrade picture itself, which I've been documenting over the past week or so. It's not pretty either. Ultimately, Windows 7 is great. But paying for it--and actually performing the upgrade--can be painful.