Maintain often, maintain early...
Yes, that's the way a Gentoo system wants to be handled. I know, I know, mine has been out of normal order since a long time. And it wasn't that bad actually.
Still: Maintain often, maintain early!
It will save you lots of trouble. And though it might seem very annoying, it actually is exactly, why you use a Gentoo-system - to know what's going on under the hood...