I haven't given a lot of thought about the optimal ordering of Democratic primaries, but I think I tend to side with Drum if for somewhat perverse reasons.
First, it is true as he says that the reality is that a good candidate has to be good at raising money and manipulating the national media, so it makes sense that good candidate training would require them to do just that in the primary. Having said that I really don't buy that Iowa and New Hampshire are all about making nice with voters at a neverending stream of diners. Iowa's about getting local political leaders who run the caucuses on your side, and New Hampshire's won in the media just like everywhere else, no matter how many times I see narcissistic voters from that state talk about "how they won't make up their minds until they meet the candidates..."
Still, I have hopes and dreams that both paid media and free national media will decline in their power to shape elections. Raising the effective price of running a primary campaign using traditional means might force candidates to get creative about other ways of campaigning, particularly by creating and mobilizing volunteers. You can't knock on every door in California, but your volunteers can.