/g/, the technology troll board of 4chan, has a meme of "install gentoo" whenever someone says "which is the best distribution to install for a new user?" Those users usually come back about a week later hating
everyone for putting them with such a difficult OS. Calculate Linux has effectively removed most of this barrier, though, making Gentoo really easy to maintain for newbies.
The Gentoo Handbook is an amazing tool to learn linux. By the end, you have an expert's understanding of how Linux works, and how to install it without a GUI (or even a package manager). I learned it during the "Stage 1 era", when the install started with bootstrapping, then building your compiler before installing the rest of your system. Nowadays, you partition disks, format, chroot in, set timezone and encoding, untar the stage 3 tarball, emerge --sync, build your kernel (which is the hardest part), install a bootloader, install wpa_supplicant, and you're done. It's about 30% more difficult than an Arch install, becuase you probably will screw up your first kernel configuration and make a nonbooting kernel, booting to a black screen. But unlike Other OS's and distros, when it breaks in Gentoo, it's probably your fault.
I have way less headaches, because chromebooks are braindead to deploy this way. flash a bios, and then install the binaries once booted off a LiveUSB. Quickpkg allows you to make binaries of your existing system (built for Sandy Bridge, until I decommission the C710's, then I'll build for haswell) with all your custom flags already set, so VLC and other apps are far more robust than their Ubuntu/Redhat versions. Gentoo is also the only distro other than GalliumOS that actually has working Elan touchpads for many chromebooks (thanks to Hugh Greenburg of GalliumOS's patches that I'm maintaining for newer kernels), as the patches have not been included in Arch or other distributions's kernels.
I run a Poettering-free install (JACK instead of PA, wpa_gui instead of NetworkManager, OpenRC instead of systemd), so having one master install I can re-deploy in the amount of time it takes to brew coffee is pretty handy, especially considering de-poetterizing a new Debian/RHEL/Fedora/Arch install is painful, if not nigh-impossible, and at the very least time-consuming.