The free software movement and FSF in particular has always been very clear that free in this context does not mean that projects can't sell CD's with software

The free software movement and FSF in particular has always been very clear that free in this context does not mean that projects can't sell CD's with software on it. It is also this interpretation that allow for paid support, which would otherwise also not be "free". It is possible that courts would make a different interpretation, or that free access to software will be interpreted as not free software, but instead about free access to a distribution channel, Which mean wordpress could go proprietary under that statement (free access to download would says nothing about freedom to run it). The distinction gets generally refereed as "free as in speech, not free as in beer". Regarding Debian, I don't know if the Debian package has anything hardcoded to wordpress.org. The generally recommended update path is to use debian package manager rather than internal updating mechanics. Debian maintainers often patch thing or change defaults as part of the packaging in order to make software behave nicely with the debian eco-system.