Debian is a remarkable mix of contradictions. Debian has a remarkable package management system, probably the best linux package management in existence. At the same time, the political battles are unbelievable frustrating and threaten to marginalize the package. Recent resolutions to remove all non-free documentation and firmware from the install mean that Sarge will be delayed until 2005. Woody, the last release, came out in 2002, which means that people using the "stable" (i.e. Woody) branch of Debian have packages that are all several years old, which is a problem for some of us. Now, I realize that anyone can simply can upgrade their installation to "testing" (i.e. Sarge) quite easily, but the fact is that most casual users won't do this. Plus, part of the "cool" factor of any distro is having reasonably up-to-date packages.
That being said, I just did a major reinstall on my home box using Sid, and I am once again floored by how easy it is to maintain a Debian box. I have a hard time using other distros now, since Debian is so effortless.