I've been running most of my company's core services on NetBSD/
i386 for close to five years now, and have been very happy ---
except for one thing: the administrative overhead of upgrading.

I run my machines conservatively: always an official release,
never -current or a snapshot, and usually not the most recent
official release, even.  And I manually install security or other
critical patches as needed --- and it's this that can sometimes
get frustrating and time-consuming, especially compared to what
people who run FreeBSD or Debian tell me about how easy it is to
"track stable" with the administrative tools those OSes provide.

Am I perhaps missing something?  Is there some sysadmin tool for
substantially automating the tracking & installation of critical
upgrades to a release that I've simply failed to discover?  If 
not, do people have homebrewed solutions to this problem?  Or
does everyone else running NetBSD in a conservative, production
setting just roll up their sleeves and do it the hard way too?

---Alex