I don't think this is a deficiency, but an inherent property of powerful type systems. If you make them very expressive, then you can not have full type checking at compile time. On the other hand, if you restrict them so that you do full static type checking, than they are very limited.
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It's a natural limit – but it doesn't make it easy to figure out in advance when it is/isn't permissible to do what you want to do. (Now, if C had type inference...)
I am not sure I agree. What is allowed by the typing rules should always be clear. What may not always be clear is whether you statically get an error during compilation or only a run-time error. But considering that we now randomly get silent miscompilation which may or may not cause a run-time problem, if you cast a void* to the wrong type, I think this is a clear improvement.