Nothing can touch gentoo when it comes to keeping an up-to-date linux system. It has the tools (emerge, dispatch-conf, elogviewer, etc.) to tell you what has changed since yesterday, get the changes, and integrate them into your system. linux is a crazy-assed pile of mismanaged bits that are freshly broken in a dozen ways every single day. Anybody that runs a linux system will…
- spend a not-insignificant amount of time keeping their system running; and…
- tell you they don’t.
It’s part of the whole cocky “look what I can do” competitiveness built into every geek. Go ahead, now it’s time for you to lie to me and tell me otherwise. 
My current strategy for staying on the back of the bucking linux bronco…
- Run three machines: bleeding edge, desktop, server
- Update the bleeding edge every day, to “learn” (Note that I do NOT run unstable releases, but trust me, your configuration will get broken as software is “upgraded”…)
- Update the desktop, only with what you need, when you want the latest “tool” (dependencies should get updated as you go)
- Only run the essentials on the server, and update every 6 months (less means you’ll get too out of date, more means you’ll be broken too often)
On my bleeding edge machine, I update the entire system every night. Then I run a script to (re-)pop up dispatch-conf in a terminal, and elogviewer in an X window, so that when I look at the machine, I have an immediate summary of configuration changes and what I need to do to update.
UPDATE: I’m adding categories for each of my gentoo machines, to track cascading configuration changes. Check out my groovy icons!
