Strange analogy considering that RMS got to where he is precisely by finding nails to hit much, much more than occasionally, and much, much more than most hammers.

I think it hits perfectly. He espouses that almost every vendor everywhere is doing something immoral and it will inevitably be used against you. Eventually, some of these predictions come true enough for some part of his audiences.

I don't think you've made a point about his abilities. I do think you've restated his proclivities, which reinforces the basis for the quip.

The analogy works if you think of RMS as a nailgun.