Heh, I'm not actually sure whether Nathaniel meant to invoke Eric Raymond's hacker emblem on the book cover or not. The grid is there, and the glider orientation is right, but the cells are squares and not circles. That orientation of the glider is kinda canonical, independent of the hacker emblem -- e.g., it's the phase that shows up in the "glider" LifeWiki article.
I emailed back and forth a little bit with Eric Raymond when the hacker-emblem proposal first came out, but I don't remember that I had anything very interesting to say. Mostly I was hoping to get the Life Lexicon factoid about the unix oscillator into the "Anticipations" section on the official Hacker Emblem page --
Unix: ... The name derives from the fact that it was for some time the mascot of the Unix lab of the mathematics faculty at the University of Waterloo.