The problem here is that Stallman has alienated so many people in his quest for the perfect GNU operating system that even those that agree with many of his ideals are less inclined to cooperate with him as they've felt his sting.
Sure, Debian includes methods, out-of-the-box, to install not-free-as-in-GPL software, or for stub installers that then pull in not-GPL software, but idealism and the realities of being stuck using proprietary or other not-GPL software will inevitably collide at the distro level. Instead of working within the realities of things like Java, Flash, and various document formats, where one can seek to get replacements, Stallman attacks the project as being against what he stands for, when in fact, in this case Debian was probably the closest thing to what he's stood for that actually attracted enough users to be relevant. Debian has even worked on Hurd, and seems to still maintain some Hurd stuff despite Stallman, rather than because of him.
Stallman seems to forget that for all of these wonderful developments to occur, people need to be able to support themselves financially, and getting paid to write software is probably the most effective means by which to get software created. There needs to be a clear division where it's acceptable to have commercial software that runs on GPL platforms, but I don't see him accepting this distinction. Certainly vendor-lock-in is not a good thing, but enforcing free software to Stallman's level is not a good thing either.