The more irritating thing Microsoft does is churn on their SDKs. I think there are at least a half dozen different ways I can generate a SOAP client from a WSDL, for instance. Or some of the abortive and competing UI layers; UWP vs WPF vs WinForms vs ATL vs MFC and so on.
Silverlight was probably the most painful. I've known some companies that made big bets on that technology, and most of them were caught flat-footed when it was announced that it would be discontinued.
Silverlight was probably the most painful. I've known some companies that made big bets on that technology, and most of them were caught flat-footed when it was announced that it would be discontinued.