Jean-Louis Gassée (author of this piece on Mossberg) is one of my favorite commentators. He's just enough of an insider and yet also an oddball, which means he keeps it pretty real in an area that tends to be an echo chamber of fawning cultists.
Dan Gillmor did a lot of very astute writing (not necessarily just reporting, but also commentary) about many aspects of the scene in SV when he wrote for the San Jose Mercury-News. He didn't seem to care much for gossip or writing purely about personalities, and was more interested in cultural and legal effects of new technologies. I believe he's now occasionally writing for the Guardian, as well as teaching journalism at the university level.
