IMHO, LibreSSL was doomed to "fail" by the mere fact that it was not picked up by Linux distributions to replace OpenSSL, the same way that x.org had replaced XFree86. Linux's influence's simply too big. LibreSSL will survive in the BSDs, and OpenSSH. That is, until OpenSSH's forked for whatever reason and the fork becomes the standard ssh on Linux distributions. I fear that's inevitable (cf. zfs).