Well... I don't think we have enough info at this point to know what's Craig *really* up to... For one thing, we NEED to know how much he is and has been *profiting* from craigslist... (as the owner of a sizable chunk of it) and how does it all play out in the long run (what may *look* like not maximizing income at this time may well be an illusion that will be dispelled in time since it appears that the long term picture is very different).
As to "giving extensively to charity," again... we NEED to know how much he *profits* and has been profiting from craigslist... and how much he gives (I'm not aware of substantial donations, given his estimated *profits* -- I'm NOT talking *salary*, that's just a red herring...).
P.S. I might have been impressed with Craig if he would have been for real, if he would have either kept craigslist a non-profit (and used the profits to pay for things like customer service and improvements, instead of pocketing them while in the same time talking the grand talk... which seems to be what's going on) or at least voluntarily disclosed his profits so people could see what he's made of... The fact that he doesn't do that makes me think he's full of hot air... (probably much more so than Larry Ellison and pretty much all those who were upfront about wanting to make money).
P.P.S. Oh... and he no longer drives a Saturn (not that it matters much...) D.