I posted my current approach to keeping my Gentoo boxes up to date on the Gentoo Forums. Just linking here for anyone on Slashdot who might be interested. The general gist of it is using GNU screen to try and make some of the update process a bit more automatic.
"Necessity is the mother of invention" is a silly proverb. "Necessity
is the mother of futile dodges" is much nearer the truth.
-- Alfred North Whitehead