Not to put words in OP's mouth, but I'd guess the weirdness is in a couple of things:
1) Jimmy can go deep on some extremely obscure corners of the industry (e.g. interactive fiction movements that maybe only a few dozen academic acolytes are even aware of).
2) The occasional deep tangent. For example, I don't think a month-long mini-biography of Edward Mannock was really necessary to appreciate the Amiga game _Wings_. But then again, I loved that tangent, so it's the kind of weirdness that I can personally embrace. I'm guessing the Analog Antiquarian is going to end up ultimately absorbing that energy anyway.