I’ve never really understood the devotion of die-hard Apple fanatics.  You know the type: the ones who have owned all four versions of the iPhone, the ones who think the Apple TV was a good idea, the ones who will argue with a straight face that Aperture can be just as good as Photoshop.

I’ve often thought it must be hard to be an Apple fanboy.  It’s not unlike being in an abusive relationship; no matter how much disdain Cupertino shows for their customers, they continue to make excuses, talk about how much they love their giant iPod, and bend over when Apple launches their next annual iteration of their hot product with the ‘new’ feature they left off the last version.

But if loving Apple is like being in an abusive relationship, liking Microsoft is like being in a co-dependent relationship with someone who doesn’t even know you’re there.  In my household, I have three computers running Windows 7, a Windows Home Server, an original Xbox, two Xbox 360s, three Microsoft-branded mice.  I’m very much looking forward to Windows Phone 7, despite living through two separate crappy Windows Mobile 6.0 and 6.1 phones. I’m ditching TiVo for Windows Media Center as soon as my InfiniTV 4 tuner arrives, and I show all my friends that come over how awesome it is. I’ve come to accept the fact that, yeah, I am a Microsoft fanboy.

But since I’m not a corporate customer ordering 200 copies of Windows 7 and Office, I might as well not even exist.

There are obviously people at Microsoft who are still concerned with the quality of the product they produce.  However, it’s starting more and more to look like the company is being managed by brain-damaged accountants who have no ability to see beyond an Excel spreadsheet and the company share price. Microsoft: I still like you, but you’re making it really, really hard to keep liking you. This is why:

Windows and Office

What Microsoft got right:

Windows 7 is one of the best operating systems period.  After years of playing catch-up to Apple in both features and aesthetics, they finally managed to create a beautiful, user-friendly, elegant and stable operating system.  Microsoft Office managed to make a huge change and innovation with Office 2007, throwing away years of legacy UI and introducing the world to the ribbon interface; Office 2010 continues to improve with cloud-based collaboration and online integration.

Where they went wrong:

Vista. The truth is, Vista wasn’t a bad operating system, but considering the enormous development cycle, it should shame Redmond that they ever produced a version of their flagship product that was so underdone.  They also splintered the Windows product with Vista, introducing baffling and confusing different versions (Home Premium, Home Basic, Ultimate).

Worse than Vista’s inflated expectations and low returns, though, was the fact that Microsoft allowed itself to lose mindshare — the perception that Apple and other critics created made Vista out to be the worst abomination that Microsoft ever made — so much that it made people forget about Windows Me, Clippy, and Microsoft Bob.

Microsoft Office is still priced too high for the average consumer, and is still really targeted at businesses.  Even the ‘Home and Student’ version is priced at $150, which is a lot to ask for what amounts to an incomplete product.  And Microsoft’s biggest competitor is now OpenOffice, a free, open-source product that is making aggressive moves into schools and businesses.  No matter how good Microsoft’s product is, it’s hard to justify the cost when the alternative is $0.

What they should do:

Windows 7 is pretty damn good, but moving forward, Microsoft shouldn’t be afraid to look forward and stop hobbling next-generation operating systems for the sake of running on older hardware or backwards compatibility.  Make future generations of Windows 64-bit only, with hardware graphics acceleration required, and handle backwards compatibility through emulation and virtualization like Apple did when they transitioned to OS X.  Office needs to embrace the home and small business consumer and align its price thusly.  Office should embrace its competitor and make it easy to work with OpenOffice XML documents, so they might actually win back converts instead of souring more customers on the brand.

Xbox 360

What Microsoft got right:

The Xbox 360 is the dominant sophisticated gaming machine this generation, second only to Nintendo’s arm-flailing family-friendly apparatus.  A true gamer’s machine, Microsoft had the foresight to push high-definition gaming and an integrated, always-connected online experience and secure a strong foothold in the living room, a beach head they had nearly ceded to consumer electronics companies like gaming rival Sony.  A stream of constant improvements including several operating system upgrades and family-friendly additions like the Avatars and the upcoming Kinect peripheral show that they take games seriously.

What they got wrong:

Where to start? Rush to launch before Sony led to poor hardware design which led to Red Ring of Death fiasco and failure rate of at least 1 in 3 early 360s but possibly as high as 2 of 3 early units, costing Microsoft one billion dollars. Making the hard drive an optional accessory instead of including one like the original Xbox had. Locking out third-party accessories to inflate first-party accessory prices. Using proprietary, overpriced hard drives, and until very recently, memory cards.  Running the Xbox Live Marketplace on Microsoft Points with an uneven exchange rate to obfuscate the actual price of items. Until very recently, requiring customers to purchase Microsoft Points in odd amounts, essentially giving Microsoft a free cash loan while leaving the customer with an unspendable balance. Nightmare, rage-inducing customer service. Charging for online play when none of their competitors have the gall to do so, and this very week announcing that they would raise the price of that service. Requiring a paid membership to view Netflix Watch Instantly when no other game console or consumer electronics device (that doesn’t require a paid membership, like TiVo) does so. Countless, confusing hardware revisions and no break or reparations for early adopters. Requiring third-party publishers to charge for content unless it’s free on a competitor’s console. Horrible, abhorrent customer service (deserves a second mention). Does that about cover it?

What they should do:

Well, basically the opposite of everything up there.  All of Microsoft’s problems in the Xbox area can basically be solved if they would just do this: quit being so ass-munchedly greedy. Your entertainment division needs to turn a profit, it doesn’t need to make you another Scrooge McDuck safe full of gold coins. You may have beaten Sony this round, but think about how badly Sony destroyed you, and Nintendo and Sega before you in the previous generations. When Microsoft debuted the first Xbox, they were humble and did everything right to please the customer.  These days, the Xbox 360 reeks of hubris…and that never turned out poorly for anybody, right?

And seriously, make Xbox Live Gold memberships $25 a year.

Windows Media Center and Windows Home Server

What Microsoft got right:

Windows Media Center is probably the best DVR software out there.  It’s extensible, beautiful, big-screen friendly, and has a passionate community of enthusiasts working to improve and support it.  And it’s free with a copy of Windows!  Windows Home Server is smarter than a NAS and easier and cheaper than a fully-featured server, but it’s an excellent product and makes household file management and backup a no-brainer.

What they got wrong:

Chances are very high that you’ve never heard of either of these products.  Microsoft barely supports or promotes these products, to the point it feels like the only reason they get made is because the teams are hidden away and forgotten about, waiting for the day when some bean counter discovers them and shuts them down for good.

Windows Media Center in particular is shackled to Windows development cycles, so product improvements don’t really get pushed out until a new version of Windows is released.  Since it was first released in 2005, that means there have really only been three versions over five years.

What they should do:

Uncouple the Windows Media Center team from Windows releases and make it a free downloadable product (for Windows only, of course).  Rebrand it Zune Media Center (instead of the Green Button, make it the Pink Button), and integrate Zune’s movie and TV streaming services that already work so well on the 360.

For Windows Home Server, they really just need to promote the damn thing and work on lowering prices.  $500 is a bit steep for non tech-enthusiasts, but if they could get the price of a fully-featured server box down to $300 or lower (with sufficient storage and memory), they could dramatically increase their install base.

Other stupidity

Generally speaking, there are a few other things that Microsoft as a whole can’t seem to get right:

  • Branding: Quit branding everything as Windows-this and Windows-that.  If it weren’t for J Allard, the Xbox 360 would probably be called the Windows Live Gaming System 2007, and the Zune would be the Windows Portable Media Player 3.  It’s irritating and a little stupid that Apple has started naming all their stuff iWhatever, but people actually like the iPod and the iPhone.  There are a lot of people who really, really hate Windows.  Even MSN had some cachet before you killed that brand and turned it into — of course — Windows Live.  Please stop.
  • Talent, infighting, and vision: Speaking of J Allard, why can’t your company seem to hold on to its geeky visionaries?  Allard, Robbie Bach, Ed Fries, all three were responsible for making the Xbox into what it is today, and all three are leaving or have left Microsoft. And the stories about the corporate infighting that led to the debacle that was the Kin…yeesh.  And the Courier!  The coolest thing that Microsoft would have ever made…will never be made!
  • PlayReady and the death of PlaysForSure: Microsoft launched a great DRM initiative that was supposed to rival the iTunes juggernaut called PlaysForSure.  It enabled third-parties to secure rental games and movies across a wide variety of portable devices and services.  And it was making traction, too.  Until Microsoft came out with the Zune software and killed it in favor of PlayReady, their other, betterrer DRM management software.  Thus screwing over their hardware partners and software licensees and destroying the only digital ecosystem that could think about challenging Steve Jobs’s empire.  So…good job on that one.

Microsoft, I like your products, I like spending money on your products.  But it’s getting harder and harder to apologize for you, and it’s getting easier and easier to leave you.