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I'd like to switch from Ubuntu to a distro that doesn't hold my hand so much, so I thought Gentoo would be interesting to play with. From what I understand though, a lot of time will be spent compiling things before I can get back into a comfortable setup.

Is it possible to do all of this compilation and configuration from within a VM, and then when it's ready, be able to boot into it?

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I think you could create a Gentoo partition, mount it somewhere in the filesystem so you can access it while running Ubuntu, then chroot to it and do the compiling in the chrooted environment. That's basically what you do as part of the Gentoo installation anyway. (The installation disc is nothing but a minimal Gentoo LiveCD which you use to set up a working environment so you can download things.)

In fact, you don't even need the Gentoo installation disc at all, since you already have a working Linux environment. Have a look at the alternative installation instructions and scroll down to section 5, "Installing Gentoo from an existing Linux distribution."

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Gentoo is all good and fun, but I got tired with all the compiling.

A friend of mine had his laptop setup such that he could boot Windows and run Gentoo in VMware (installed on a partition), or boot Gentoo natively, so it can be done. I would recommend setting up the dual boot first, then from within Ubuntu setup VMware or something to use Gentoo, do all your setup, and then go back to native Gentoo.

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