I not quiet sure about how you are going to implement this. Are you going to have nested physical pages or you are going to work with the UI. I prepared a short video where I created three pages
Nested1 - inherits from Root
Nested2 -inherits from Nested1
In the Root I added one ContentBlock control with content - "test". I can see the content "test" in all templates that inherit from Root. For me this behavior looks normal. Can you provide some more description about your scenario ( just a simple wireframe/schema, short video) that will help us to understand your case, so we could see if we can come up with a solution.
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