You were running Evolution on your server ? No, just joking ...
I really do understand your issues with Gentoo; all I am saying is, it was never mine.
For any servers I minimised the packages I used, and it was very seldom that I had to do anything more than emerge -uv world.
For my home network I tend to run IDS / dark nets and honey pots because I want to and I want to know what's going on.
Yes, every upgrade is a potential risk, and yes, you have to upgrade certain packages more often than others.
But strangely enough I usually found that I don't have to upgrade it the moment a new release becomes available, and more often than not, by doing a bit of research before upgrading said important package I could pre-empt any potential issues I might have.
But, as I also mentioned, I have also gone over to use binary packaged distributions more often than not in a production environment.