I won't comment on the actual licensing discussion, that appears to have been done to death. In terms of GNU though; I've never heard that the FSD is more "indoctrined" or "rigid" than the OSD. The OSD is directly descended from the GNU/FSF outline, along the lines of FSD -> DFSG -> OSD (where -> indicates Bruce Perens at work). But, the DFSG is vastly more complex than the free software definition, and actually encompasses a *different* meaning of "software" (at least, that is current opinion).

It's not the wording, nor the "does this pass", that is meaningful - it's the spirit. One of the reasons the FSD is so simple is because it's meant to be applied with common sense. You can argue that the GPL fails the DFSG because programming proprietary software is a field of endeavor; most people wouldn't argue that it's non-free though.