I think that Craig actually isn't behind these decisions, though, which would explain the apparent conflict between his friendly attitude and the unfriendly attitude of the company overall.
The company goes to some effort to maintain that "we're almost a non-profit" angle though; Jim Buckmaster's "About" page calls himself a communist, for example:
Like it or not, Craig is basically the brand identity for Craigslist. It's going to be awfully hard for Craigslist to separate themselves meaningfully from Craig. The more discordance there is between the two, the worse it is for their brand image, whatever the motivation.
