I too am using portmaster, but mainly because I got tired of the ruby requirement with portupgrade (plus I like that it doesn't keep a different database).
I set a cron job to run portsnap (took me a while to stop using CVS... old habits die hard) overnight, which of course the output is mailed to root. I then later run a cron job that basically runs "pkg_version -v -L '='" and mails the output to root. That way I always know what needs updating, and can plan accordingly.
I don't always update immediately (unless it's a security issue). I usually check the changes at "http://www.freebsd.org/ports/" for what changed in the port, and if it's something minor I'll apply it during the regular weekly maintenance.
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I just saved a bunch of money on my car insurance by fleeing the scene of the accident!
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