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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.