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Debian has always been my favorite distro, mainly because of it's apt system and the social contract (see www.debian.org).
Debian can be as easy or as hard as you want.
Most configuration can be done by the dpkg-reconfigure system, but you don't need to use that if you want to configure your system the hard way.
SID offers lots of new software that Woody & Sarge don't, which is an extra plus for me.
Apt is simply brilliant, most people know apt now, since the main distro's are using it too now.
I started with potato and dist-upgraded to SID
(meaning all packages are being replaced by newer ones giving a new and updated system).
It's not that bloated as some other distro's as you're really in control what gets installed.
The dark side of SID has to be that packages can be broken at any given time you update as it's the developpers' version.
Most of the time it gets fixed in a matter of days though.
SID does the trick for me but I won't recommend it to someone who's just starting with GNU/Linux, but you have to try it at least once in your life