> 2. One of the things LibreSSL removes is the FIPS validated stuff. Distributions that harbor ambitions of being used in large US corporate and government installations want that.

Sounds like it could have happened if someone went to bat for it. Red Hat deciding to include it (even if they didn't replace OpenSSL with it immediately) and pushing to get it certified and the portability stuff more stable would have done this.

> 3. By the time the portable LibreSSL build system came out, there were already significant improvements afoot within the OpenSSL project.

That's probably the real reason. Although, given the stuff mentioned in that bug/talk and how much seems to have been based on extreme portability, unless OpenSSL decided to just give up on some aspects of that (I doubt it), then some of the problems (code complexity, not to mention ROP helpers) probably survive (not that I know).