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Thanks for all the ad hominem, segedunumm... I never meant to offend you or hurt you. Sorry for that, I only wanted to be helpful and give some input on my experience.
You're not offending me. I'm just curious why you're doing what you're doing, because if you do that with any distro and not just Gentoo then you're in for a rough time.
The longer you don't emerge, the more likely there are issues that can't be resolved automatically. This is a 'feature' that all rolling release distros seem to suffer from.
Well, the alternative is that you'll have to take the server down and install a completely updated and new version of a distro and you'll have to reproduce your install. Yes, rolling releases can present problems, but on a production server you should be leaving it as-is, and when you want to do a mass upgrade then practice on another non-essential server. Security upgrades shouldn't present a problem. Have a look at what any emerge will actually install before you do it.
That's what I wound up doing most of the time, upgrading what really needed to be upgraded.
I'm now deploying Debian on all my servers, and it's easier to set up, and easier to keep up-to-date (also on dist-upgrades). It's really more work to do that on a Gentoo server, but I guess for some people it's worth it. I seem to manage fine on vanilla stuff, so it's less hassle for me this way. And the binaries that I am running, are run by a lot of other people as well, which has its advantages.