Adding my voice to the chorus.
The Microsoft Windows ecosystem is a god send for those wanting to enforce single sign on, roaming profiles and group policy to control things deploy Chrome, 7-Zip or all manner of apps straight to the desktop or lock down access for say the demo room machines but give full access to engineering notebooks and enforce things like password policy, mapped network drives, etc.
It honestly just works and is fantastic in practise for companies wanting to enforce good IT policies with 10+ employees (in comparison try doing the above with Mac OS X + Mac OS X Server - like pulling teeth).
However Microsoft's licensing is absolutely fracking byzantine.
* I first need a server license - is it per socket or per core?
* Then I need my desktop licenses - do I need Pro or Enterprise? Or heck, maybe Ultimate only has the regional language options I need?
* Then I apparently need a fracking Client Access License for not only Windows Server to Windows Desktop services but for god damn DNS and DHCP services too! Like seriously MS - are you kidding me? So every iOS or Android device which pops up on our Windows DHCP/DNS needs a CAL apparently.
Now the whole cluster fudge above would be barely tolerable for any well funded startup or company IF Microsoft made buying these licenses easy.
If the above nightmare sounds bad however, just try getting licensed for it all and ensuring you're compliant.
It's seriously, a real damn shame because Microsoft Windows Server + Windows desktop is fantastic. When put together it really does work beautifully. It's just such a shame that MS seems to shoot itself in the foot consistently when it comes to figuring out their licensing.