So why the different standard?

So I’m listing to Hannity and it funny that he is getting chewed out by a lady because he doesn’t know anyone the make under 30 k a year, and that somehow his opinion about the “common man” and what they are going though is invalid because he is making money now.
So because he is making money now, he can’t understand what people that don’t have as much money are going though ?
So I think that it’s funny coming from someone that probably voted for Obama because he would help the middle class. So tell me how can someone that grew up in Hawaii and attended Harvard and then yes worked in the community but was able to buy a million dollar home can have such a good handle on the struggle of the middle and lower class?
How is it that a conservative that came from no money, but has money now doesn’t know how is like for the middle/lower class, but a democrat that came from no money but has money now can be compassionate to the middle/lower class or a Democrat that came from money can understand the middle/lower class?