Keeping mission critical machines up2date is always a burden for a sysadmin.
Esp. if you are an allround sysadmin, responsible for all kind of servers.
On freeBSD, this has become quite easy.
There has is a new tool in town: portsnap.

Setup is easy. See this article on TaoSecurity.
After installing it boils down to this:

cd /usr/ports
portsnap fetch
portsnap update
make fetchindex
portsdb -u
portversion -v -l “<”
Check /usr/ports/UPDATING for information relating to my applications
portupgrade -varR

Total control :)