I have just been looking at this issue myself, as I wish to do validation on a ComboBox whilst still using the convention based binding.
Having had a dig through the Caliburn.Micro code, the issue seems to be that the ConfigureSelectedItem routine calls BindingOperations.SetBinding directly rather than calling the SetBinding Action on the ConventionManager which applies all the default validation rules and so forth. I'm not sure if there was a reason for this, perhaps someone with a better understanding of the framework could answer that.
What it does mean is that overriding ApplyValidation has no effect as it is never called.
Having had a dig through the Caliburn.Micro code, the issue seems to be that the ConfigureSelectedItem routine calls BindingOperations.SetBinding directly rather than calling the SetBinding Action on the ConventionManager which applies all the default validation rules and so forth. I'm not sure if there was a reason for this, perhaps someone with a better understanding of the framework could answer that.
What it does mean is that overriding ApplyValidation has no effect as it is never called.