> On another note: C++ compiler should by default keep statistics about the chain of #include's / parsing during compilation and dump it to a file at the end and also summarize how badly you're re-parsing the same .h files during build.

Not exactly that, but do you know clang's -ftime-trace and tools like https://github.com/aras-p/ClangBuildAnalyzer which help analyzing where time is actually spent? (In small repeated headers I don't see much of a problem, but they of course may contain not so small things ...)