Meetings, sprint ceremonies, interruptions I've come to deal with as baggage that comes with the territory. But when I have to blow the dust off my olde Microsoft Licensing Nits and Pitfalls Tome and play license-lawyer again, that really sucks the life out of me.
Windows Server is a great product and I want to pay great money and use it without worrying about where in the cloud it's floating. Why even cut a distinction about what kind of machine is hosting your product, virtual or metal? Nevermind even talking about who owns that machine being an issue.
If that's the case, just use the windows license that's provided to you when you spin up an instance with your cloud provider. This is only for people using dedicated instances.