I hate to tell you this, but I guess it's something only an outsider can tell you... Dean is very, very, far to the left. His only right-leaning stick is he's not willing to support gun bans. He supports most gun laws, just not bans... which doesn't quite make him a gun rights supporter.
Something we've discussed several times on this forum is how people always think that their views, and the views that they agree with, are the views that most people agree with. That's why folks like Walter Cronkite, Ted Turner, and Geraldine Ferraro (to name just a few) can go before a camera and claim that they are Moderates and that their views are mainstream. The only real moderate candidate in the Democratic race right now is Lieberman.
Why does a person have to have been poor in order to understand the needs of the poor? Does a doctor need to have cancer before he can treat someone else for the disease? Should a cop have been a criminal before they can fight crime? Besides, experience with being poor is a knife that cuts both ways as a former poor person can say "I know what it's like and I wish someone would have helped me out like I'm helping others", or they can have the view of "I was poor and I got myself out of poverty. If I can do it on my own then the rest of these deadbeats should get off their a$$es and do it too."
What's really important, to me anyway, is does the candidate have the guts to do what needs to be done. What I've really liked about Bush is that he's willing to suffer the slings and arrows of the media, the protest groups, the political hacks, etc., in order to do what he believes in. He doesn't waste too much time on wishful thinking and looking at the world through rose-colored glasses. He's a black & white guy, and I like that. I like the notions of pre-emptive strikes, cancelling treaties that everyone knows are unfair to America, and looking out for the folks who pay the bills in this country.