Things may have changed, but you should take a look at Datacenter licensing. Last time I researched this (2 years ago), a Datacenter license covered an unlimite

Things may have changed, but you should take a look at Datacenter licensing. Last time I researched this (2 years ago), a Datacenter license covered an unlimited number of guests on that host. That said, I think most businesses where this really matters have an Enterprise Agreement with a yearly true-up. We're mid sized (<1000) and we have one. No idea what we actually pay, but having an EA and a working KMS infrastructure at least treats the symptoms. I guess the OS licensing is really one of the bigger annoyances though. All these guys waxing poetic about how great Visual Studio and C# and MVC.NET and whatever are, might not be singing the same tune if those products weren't being subsidized by the other components they rarely have to think about.