I'm using OpenBSD for quite a while now. All I do, however is go from one release to the next, always just doing an update. I configured the system so it works as my router and firewall, and it works quite good like that. But, I never update packages. All I do, I just move on to the next release.
Coming from the Linux world, I'm used to apply updates a few times a week, but how do I do that on *BSD? - Or is this not part of the *BSD philosophy?