Siegler exemplifies the syndrome that nearly all the high profile tech journalists have sealed themselves into an Apple-centric tech-bubble in San Francisco / bay area. There was a TWiT episode a week or two ago where every single panelist confessed to exclusively using an iPhone and Mac, some having not touched a PC in years ... yet here they were trying to sound informative on Android and Windows, the actual dominant technologies in "reality". They've basically dealt themselves out of being able to be informed and balanced on tech topics by refusing to use anything not made by Apple and now don't even understand when people accuse them of being unbalanced.
It all depends which part of "reality" you focus on. I doubt that Windows is dominant anywhere where interesting stuff happens: be it HN, or developers' conference (save for .NET).
As for balance: this goes both ways. However it is much more difficult to find someone with no experience of Windows (I've used MS products for 15+ years before switching and still have Windows VM for testing) than someone with no experience with OS X. Somehow that does not stop the latter crowd from talking about walled gardens, form over function, „it's all marketing“, computers for non-techie people (it's UNIX, are you kidding me?), hipsters and gays, etc.
Actually, I perceive it too. Most Windows developers I meet are doing either Java or .Net - or, even worse, SAP, Oracle or... maintaining legacy VB client server/stuff. That's not a place you would expect interesting things to happen.
At least, not for me - I focus on dynamic languages, web frameworks and distributed databases - the interesting stuff can usually be coerced into running on Windows, but it tends to involve things like Cygwin or VMs. If you have to use Cygwin or a VM to do your job, you are really running the wrong OS for the job.