Sure, a lot of sysadmins in the Microsoft area would be well advised to get a clue. I'm sometimes frightened about how easy (a lot of) those people perceive it to set up and maintain a network, or a mission critical database. Those are complex systems, which don't get any less complex by GUIs, Wizards or dancing paperclips.
However, shifting the blame on the admins for not being up to date is a cheap excuse for a security architecture which is flawed from the core. Although it might get a little better with XP (I won't know, W2K is the last MS-OS I have on a laptop partition and it will remain that way, forever or until to its deletion, no DRM shit for me), Microsofts fundamental security problem is to ship-now, patch later.
Now, this might be fine for individuals with a lot of time on their hand and a broadband connection. For corporations it's a nightmare, because
Patching your machines once a month is a good job, patching them weekly is extremely brave and patching them daily is just outright impossible
Microsoft is not known for it's quality control in the patching department. Through the massive, everything interwired (not to say horrible) architecture of Windows, each and every change is a risk. As we all know (cough!) IE is a vital part of the operating system. Personally I don't care to have my database corrupted, or my OS re-installed, because some MS-programmer heard his managers whip cracking, if he didn't get it out the door fast. Sure, every patch for every OS has risks, but Microsoftys abyssimal track record (NT Service Pack 6, or the Office patch which prevented office to start at all, anyone ?) would make me as a sysadmin extremely weary, to install an untested patch from our Redmond friends.
Even worse, you deal in a blackbox environment. Having applied a patch to 19 machines successful, does not mean that it will work on the next one. And it's likely, that you hardly have a clue why this would be.
There are a lot more reasons, but you get the picture.
Further, it might be a sort of Direct barell of pump action to your foot, pull trigger. If it doesn't hurt, try again... action by Microsoft. Here's a hint: "You are alienating and insulting your sysadmins". A lot of them, especially the good ones, won't like this much and might start to work against MSs interest. Maybe even by such depictable actions like starting to install a few Linux boxes behind their managers backs.
The same managers reading a recent Gartner Group report. A report that has not many favorable things to say about a Microsoft core, server product. It is understandable that the manager carefully locks his office door, opens a desk drawer and takes out a bottle of Vodka, which he keeps there for real emergency situations...