I have no doubt that he has probably more experience in interacting with normal people. However, it is simply not the same. The rich are different, take my word for it. In particular if they come from a family that is secure in their ordinate wealth. yes they can go and experiment in the "real" world. But they are secure in the knowledge that if things go wrong they can always go back into the cocoon that is their family.
I have been around wealthy people most of my life. They have a different culture and sociology than the rest of us. An incident comes to mind when I was accompanying a friend of mine whom I had gone to school with (married into the Dupont family) on a visit to Harlem. He was commenting to me how he was familiar with what black people and working class people go through in general because he visited often. My comment to him was (we'll call him Henry) "Henry, you're just a tourist, you haven't got a clue."
Henry you see, will never have to worry how he'll pay his bills. Where his next paycheck is coming from, or whether he will still have a job that won't be downsized or outsourced. That is a set of worries that GW has never had to contend with either.
Many wealthy people know what it's to lose jobs and some make certain that they raise their kids to know what it's like to be " joe everage " too. How ? They make them get jobs and pay some of their own way.
I've known a few myself. Some are elitist snobs. Many aren't.
Moreover, I know several people who have worked directly for and with GWB before he entered politics. In their judgment, which I trust, GWB is a genuine guy -- without an elitist bone in his body.
You can sense some of this for yourself, in GWB's reaction to the academic and student environment at Yale and, in particular, at Harvard. Plus, what other FReepers with personal experience have remarked about his career as an independent oilman in Midland.
Elitism is the crux of what you're objecting to. But not all wealthy people are elitist. Nor are all people of modest means humble (see acadaemia).