How do you all manage keeping your server updated? I'm not a sysadmin or someone that is on my linode every day. I might get on it once a month and run apt-get. Does anyone have any tips or tricks for making sure I'm keeping it updated from a security perspective? None of my sites are mission critical (mostly wordpress) and so I've considered setting a cron to run apt-get update and apt-get upgraded on a daily basis. Is this a bad idea?

Any better ways to do it?

I'm not a fan of automatically updating - in some (admittedly rare) cases, things can break. I prefer to see what's happening.

On CentOS, I have a cron script that runs yum check-update and e-mails me if any updates are available. Not sure what the exact equivalent would be on Debian/Ubuntu but I'm sure it can be done easily.

you want apticron, run:
apt-get install apticron

that will run from cron daily and email you if there are any updates