> I'm pretty sure even OpenBSD packages OpenSSL in ports for third party software, since so many pieces of software basically require it and do not work with LibreSSL anymore.

Theo Buehler talked about the current status of LibreSSL compatibility at EuroBSDcon last week. To take some quotes:

“> 2000 OpenBSD ports link against libcrypto or libssl” [i.e., LibreSSL]

“< 100 of these need patches (< 5%)”

“6 ports link against OpenSSL”

https://www.youtube.com/watch?v=bF1d_aCSzS0