I've used FreeBSD since the mid nineties (it's what I cut my teeth on, Unix wise). I've also been using Gentoo images over at Rackspace for a while now. From

I've used FreeBSD since the mid nineties (it's what I cut my teeth on, Unix wise). I've also been using Gentoo images over at Rackspace for a while now. From a basic standpoint, the two are the same - one command and off it goes, with a well thought out set of "pre-cooked" installations ready to go. However, I have to give Gentoo credit for being a bit smarter about dependencies. On the other hand, the structure for the actual portage tree is....less preferable than FreeBSD's layout for the ports collection. Also Gentoo's portage can "mask" certain builds, basically deprecating them in a way that's really hard to turn off, and that can get annoying at times.