I think at some point, if you've got a legacy application running on such an old platform, the cost of maintaining your own fork of libraries like OpenSSL has to fall on you eventually.

Although OpenSSL themselves continuing to maintain these ancient ports is admirable in a way, the unmaintainability it has caused to the code base as a whole is a serious problem that has reduced security for everyone.

Every horrifying thing in there is justifiable because "someone might be using it". Not enough reason to risk the security of every net-connected Unix over.

When you want to make idealogcal changes to an existing codebase that does not mesh with the idealologies of the maintainer(s), forking is a great way to make your changes happen. Time will tell if your ideas were good ones. That and how well your maintain and promote your fork. :-)

In the case of OpenSSL vs LibreSSL, it appears the OpenBSD team made a great call and they are making it work really well. As for if anyone else agrees and adopts it, only time will tell.