That's not really true -- in practice, most companies have a volume license for production machines, and a single MSDN subscription includes as many licenses for development and test as you want.
I'm not advocating that anyone use Windows, just saying that in practice licensure isn't as hard of an operational problem as it might seem. The price still hurts, though.
Honestly, admin on Linux is not that hard, and server most tools out there were designed for linux first, and Windows instructions are often of poor quality or lacking entirely.