How does cid make power?

I think you just answered your own question here unless I am missing something. In theory, based on your math, if a 100 cid engine is capable of 550hp, then all things being equal, an engine that is 3x the size is capable of 3x the hp. 300 cid engine is capable of 1,650hp.
I want to see the 300cid engine that hold itself together while making 1,650hp N/A

Not really if you 3x the cid with same top end (heads cam etc..) theoretically just move the powerband down about a 3rd of what it was. You would need to triple the airflow.