I think the problem goes even deeper..
Interesting article and I can most certainly relate to all this. I'm currently using 2 in-house Windows 2003R2 servers and one 2008R2 for an ASP project and we ended up with the same conclusion. There are so many loopholes and uncertainties; it even seems as if the Microsoft sales agents also have no clue other than to advice you to go for the most lucrative licensing scheme (lucrative for them of course).
It's depressing, especially if you're actually interested in the environment(s) and the technique.
But the bottom line is quite simple really: Microsoft doesn't know how to appeal to the masses. You would think that after so many years with several competitors around (even those which cannot be bought) they'd smarten up, but no. There have been some very good moves (some commercials are very slick, some of the new features are very well designed too, etc.) but those are merely bits and pieces. In the overall it's one unappealing mess.
Think about it: this is yet another situation in which their TechNet environment might have been able to help them (to a certain degree). For example; I hope we all know that TechNet is/was all about systems administration; you could lay your hands on pretty much anything which Microsoft provided and use it in test labs and such.
They could have raised the bar a bit I think. Provide a "TechNet virtualisation" license which allows subscribers to use an x amount of specific client / server products within a (fully licensed) Hyper-V environment. It may certainly appeal, it makes things easier and the most important thing: it would generate more steady revenue for Microsoft.
Bet they never thought of that, not to mention having little options left considering how they're going to whack TechNet instead of extending on it.
They need to make it easier for the masses, not harder.