Olive's argument seems to boil down to that, in order to avoid annoying people, Debian should - allow consessions (new restrictions that do not benefit Free Software; that is, a one-way exchange), if they appear "minor". This is a chipping- away at the standards of free software, allowing more and varied restrictions to be placed on users. The burden of proof needs to be placed squarely on the people wanting to restrict us: explain to us why we should accept the new limitation, and how it benefits Free Software.
You seem to say that if a given license has conditions that would best be removed to benefit free software then the license is by itself non-free. But Debian does not choose the license of a given software; it just choose if will include the software in main or not. The question becomes if it would benefit free software if the given software is included. With this point of view including GFDL manuals in Debian would benefit free software since rejecting it would make a lot of free software unusable. The GNU project have accepted non ideal free software license on the same basis (for example the TeX license).
Anyway, Debian will most probably continues to include GFDL and other non-ideal free licenses; it will just put these softwares in non-free. This will encourage more and more people to adopt software in the non-free directory (since you are in discordance with both the FSF and the open source movement; these people will include people from both movements) and will make the distinction between main and non-free pointless.
For software copyrighted by Debian; things are different since in this case Debian can choose the license. It must then follow a stricter policy and avoid non-ideal license. This is once again what the GNU project have done (with the exeption of GFDL which is not ideal): GNU software are (L)GPL but consider as acceptable other licenses.
Olive