Debian testing is reasonably up to date, updates continuously and requires much less maintenance than Gentoo. It's about as hassle-free as Ubuntu. Ubuntu does have some useful PPAs, but if you pick the right version, you can just add an Ubuntu PPA to Debian and it will work.
I could live without some of the political aspects of Debian (there's no Firefox in the default repos???), but they are really just minor hassles. Import a couple PPAs, and you are rolling.
For those of you looking for an alternate distro, my shortlist was Debian Testing and Arch Linux. Arch does look like it has a killer community: techie and helpful, lots of available documentation, much like what I remember from Gentoo. Debian won because I'm less inclined to workstation tweaking and more inclined to real work nowadays.