I used FreeBSD and OpenBSD for a while, and what drove me back to GNU/Linux was package management. OpenBSD was OK at it even if it had a limited selection, but I never had much luck with FreeBSD ports. Having a nice, stable base system wasn't very useful when ports were always being updated to the latest version; if I wanted a security fix, I had to take all the feature changes and new bugs, too. I tried a bunch of…
Also, in 7 years, I've never had package updates break things on OpenBSD (aside from config file formats changing or postgres database transfers, with warnings at update). That happened to me a couple times with Debian (around woody).
* except for my ports that haven't made it upstream yet.