The answer is that VS does not type check default values for VB.NET, regardless of OptionStrict or not.
<DefaultValueAttribute(False)> is valid because the attribute definition is really a constructor and not a type definition, as such it's type is DefaultValueAttribute and not a return type of boolean. Furthermore the .Value property of the DefaultValueAttribute is of type Object and hence it's type cannot be compared either, as such the very existence of DefaultValueAttribute violates Option Strict On and hence Option Strict ignored for the scope of DefaultValue Attributes.