It may, but then, the ultimate test, as you have yourself made clear, is whether the definitions uphold the four freedoms. There is a tension, possibly irreconcilable, between the idealistic criterion, the four freedoms, and the pragmatic criterion, that some systems must fit. It may well be that no current system upholds the four freedoms.
As one who has Emacs on his desktop every day, I’m quite sure I bought the analogy 
Well, when the OSD was written, it had 12 years of actual experience behind it, and every part of it was based on real, practical experiences of deciding whether a package should go into Debian or not.
That’s obviously not a luxury we have today, but it is very clear that it is easier to start narrow and allow more to fit, then to throw things out.
I have a problem with the waterfall methodology here, one shouldn’t think that the definition can be written in stone. One should assume further iterations will have to be done going forward. I certainly see a problem with the assumption that there is a data set and that has to be open, particularly around federative learning, but I also see that OSI is not able to tackle it at present.
“kicking problems down the road” is negative just because you are not prepared to iterate, if you designed the process for iterations, then it wouldn’t actually have been bad.