It seems to me that your kernel issues are more related to your predecessor's failures as an admin than to Gentoo. Nothing you can do on Gentoo can't be done on most distributions, including poorly-done kernel upgrades.
I've administered a few gentoo machines a few years ago and can attest that it's a major PIA. Or let me elaborate a bit, system failures that happened on gentoo didn't seem to happen on other systems, system failures that also happened on other system took significantly more time to resolve and required much deeper knowledge of system internals than debian, centos or whatnot.
When I finally moved everything to debian and my time spent on system administration tasks went down dramatically.
It seems to me that Dobb's predecessor failed to understand what he was doing and therefore failed as an admin. If Gentoo required a level of understanding which he did not have, then he should not have been using Gentoo. That is exactly the reason I switched; I realized that I needed to spend time with other distributions learning more basic elements of Linux systems before I would be capable of adeptly administering a Gentoo system. In the hands of those more experienced, however, distributions such as Gentoo (or Slackware) are powerful tools.