Yes you always need skilled people but the path from on-prem Windows guy to Azure guy is much shorter and easier than the path from say on-prem Red Hat guy to AWS guy.
I don’t see how being a Windows guy makes Azure easier to grasp. It’s mostly not even Windows you’re interacting with.
Because you’re already familiar with the Microsoft ecosystem and they have invested a lot in making it a smooth transition. If you know C# or Powershell or use Visual Studio and watch Channel 9 and know your way around MSDN etc etc etc it’s all the same. Whereas AWS is a cold start and uphill in comparison.