It is very difficult to give one single answer, to your first question, without knowing the context about which you are speaking. First, how the 20ft. head of air is created? Secondly, does the air column has any pressure or vacuum acting upon it?
You should mind that when a liquid head creates pressure on its bottom, there is atmospheric pressure acting on the vapor liquid interface. But for gases, it is only atmospheric pressure.
Answer to your second question is 'No'.
If I ignore what I said above, approximately, you can calculate Pressure = (head x density of air)/2.31
Regards,