Another issue is that, at least in my experience, the upgrade experience can be a bit fraught. Especially if you're using packages. I've been using FreeBSD intermittently since somewhere around 1997 or 1998, so I'm not a complete n00b. But I've had enough instances where an upgrade hosed something important that I'm hesitant to upgrade until I'm sure I'll have time to troubleshoot fix something weird and new. And this of course ends up being a self-fulfilling prophecy because the longer I wait to upgrade, the more likely stuff is to break.
I don't think I'm an idiot, but sometimes FreeBSD makes me feel like one. (This is, of course, in contrast to OpenBSD where the software may not make me feel like an idiot, but the developers do.)
I can add that I have experienced upgrade problems firsthand while running FreeBSD on Digital Ocean. In my case, rebooting after an upgrade would hang.
Yeah, I had that bug too (or another one that caused similar behavior). Great fun.
Edit: I realize my comments may sound a bit unfair. I don't want to come across as saying "they had a bug in their software, so they suck!" I realize stuff happens, and these are complex things. But I'm bothered by the fact that it has happened often enough that I'm actually nervous to upgrade my FreeBSD system, even though I have been using the OS for 20 years and did time as a professional sysadmin. I guess the flip side is that once it's working, FreeBSD is so stable and drama-free that my incentives for upgrading are very low unless there's a critical security issue.
I am an extremely casual FreeBSD user. I also happen to be an obsessive compulsive software updater conditioned to systems restarting and coming back after a few minutes. So this hanging thing had me completely baffled. It was also my first time ever looking at the Digital Ocean console.
I don't think I'm an idiot, but sometimes FreeBSD makes me feel like one. (This is, of course, in contrast to OpenBSD where the software may not make me feel like an idiot, but the developers do.)