I'm curious what circles you run in in the open source world. In my little corner of it, most everyone had nothing but excitement and support for LibreSSL.
While attending a security conference in Vancouver earlier this year, someone commented that they thought the OpenBSD team was childish for forking LibreSSL, and several people chimed in with agreement.
Of course this is all hear-say for you, and your experiences may vary. I've met more than a handful of people who did not like the fork. There are lots of people in the world, and they all have different opinions.
I suppose that this attitude comes from people who think the fork happened solely because of Heartbleed, when the real reasons are a little more intricate[0] but the straw that broke the camels back was the discovery that OpenSSL had known about certain bugs and let patches to fix them rot in their bug tracker for years. It's hard to contribute changes back when a project won't take patches.
OpenSSL could have taken LibreSSL's changes if they wanted to, it's all public in the OpenBSD source tree, but they haven't.
The OpenSSL developers would have a much tougher time dropping MSDOS and VMS and OS/360 support because there are still a couple of people who need it.
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.
Problems are easier to spot when there are less underlying assumptions.
If you don't, people still clamor for legacy support and bug-for-bug compatibility. A fork is the only way of truly signalling "We aren't going to support our old mistakes anymore."
New features don't need forks, but cleaning up raging stupid and cruft does.
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.