I think it could become a very dangerous time for Microsoft where their server products are concerned because lets be honest: most products don't really look very appealing at all. Although it shouldn't but "eye candy" matters, at least to some extend. If that weren't true then how come we gained so much when looking at Windows 7 in comparison to, say, Windows 2000 or Windows XP?
And on servers, especially those with a graphical user interface, some people will expect to see an environment which will at least look somewhat familiar. Its what has been happening over the server lines for over the past years anyway.
Well, I don't have to mention how great Windows 8 is going, and the new server line basically follows the same path as the client. Including the addition of all the touch crapola. If people hate it on the desktop, why would they embrace it on the server-side? I personally think you'll get even more resistance on that front.
Another problem: once a new product is out, good luck getting the previous one! Windows 7 is more or less still around, but trying to get Microsoft Office 2010? Or what about server products; Windows Server 2k8 is pretty straight forward, but these days 2012 needs to be pushed forwards making 2008 nearly impossible to get.
Which poses us with yet another problem where "eye candy" is concerned. Windows used to be all about providing us with a detail rich interface, which really looked pretty amazing. Of course also taxing on the hardware, but lets ignore this for now.
So here we are; and what is the current development all going to be? Making the interface as flat and minimalistic as possible. Each to his own, but the modern products look extremely unappealing to me. Starting with the often flat and boring icons, right down to hard to look at screens (such as the new MS Office products). And since the server products follow the clients...
If people hate the clients (think Windows 8) why would they bother looking into a server which follows the same idiocy? (something I never quite understood; why make developer and server products follow a consumer market? isn't it fair to say that functionality should have a higher priority than desktop styles?).
My take? Open up the sales of Windows server 2008 again, and I think you might be surprised at the results. Same applies to the Office products. I know for a fact that plenty of people would rather buy Office 2010 than getting their hands on the new stuff. And I think the same (to a certain extend) applies to the server range as well.
Alas; for me & my (small!) company its already too late. We started a full transition into FreeBSD and so far things are looking pretty good. Solid support & documentation, nearly every piece of software is provided; both open source as well as commercially licensed products (Ports collection) and best of all: with the help from the Mono and Samba projects you may very well end up with a better Windows-like server than the original!
So far we never looked back.