Comment by BeetleB

Yeah - in the past if you waited say a year before doing an update you had a serious risk of incompatibilities that Portage couldn't fix (the intermediate "bridge" packages were no longer in the tree, etc).

I would often go several months without an update and occasionally ran into this issue. So I committed to doing an update once a month.

I'd never use Gentoo at work unless it was a very dedicated server with only a few items installed.