Alex Payne writes online here.

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Remote Install Insanity

A recommendation: don’t try to install an operating system over an existing, running operating system (from inside that latter operating system) on a remote machine.

We got a dedicated server for work projects and our provider doesn’t offer Gentoo Linux, far and away my server OS preference. However, several of their customers have successfully installed Gentoo remotely over existing Red Hat installations, though not without much frustration. My attempts to follow in their paths were not readily successful, and I don’t have the time to spend getting things working (and placing reboot request tickets with our provider’s admin staff). It looks like the box will end up with FreeBSD, which our provider does support. I don’t mind working with FreeBSD; Gentoo follows the BSD model in several ways, so FreeBSD is a closer second than, say, Red Hat Enterprise.

So, the moral is: no remote installs, and collocate pre-installed boxes in the future. It was worth a shot.