This is an OS which has everything. It's clean, it's simple, it has a helpful community, stable code, and even pretty good package counts to support nearly any desktop/workstation activity.
And yet, I feel like there are nagging issues which ultimately affect all non-mainstream^1^ OSes. Display driver complications, janky system upgrades, a lack of groupware clients. I'm not picking on OpenBSD, I love the distro and I think it should succeed in this particular area (the desktop/workstation) where other open source alternatives have failed, but why hasn't anybody managed to make it happen yet?
For a while, there was a similar hope around DragonflyBSD in the FreeBSD community, but I don't know where that ended up... I do know I see nobody really using it.
What's it going to take?
^1^Obviously, I mean MacOS and Windows, since Linux is at least as hampered on the desktop, perhaps moreso on account of the poor community and scattered vision.
Curious what upgrade methods you used.. sysupgrade is pretty painless.
I've found sysupgrade to be pretty good at the core OS, but I have definitely had issues with drivers (particularly audio and display) and third party packages installed through pkg_add. Upgrading seems to be a mixed bag in terms of continuity of function when you're running a richer system, as a workstation often is. On a server, with minimal package surface area, things are just fine.