I am not able to handle "somewhat complex situations" at all,because I am a non-technical person who only is interested in using free sofware and I am a sidux user since January 2007. I am able to read thought, and so I never experienced any complications at all. I have a look if the dist-upgrade wants to remove packages, if that is not the case, I upgrade.
What I like in sidux is the community and that it is really fast and I like very much Debian's big repository (for example, neither in Suse nor in Unbuntu I found Noteedit or Lilypond.
I am very thankful for the people who do this fine work!