How often do you drain your air compressor?

YEP, including every compressor manufacturer that feeds the pump output straight to the tank via a check valve.
My setup goes through two tranny coolers with 12volt fans powered off of the 220 motor per leg. ( 120 to 12v converters.) switched by pressure switch. Then after that cooling it goes to this style setup.
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I have much longer drops to catch the water than this. Maybe 16 inches.
I am talking about the bottom of the loops with the drain valves. This drop will be where the water collects. It needs to be longer..

So after all this, THEN, it goes to the tank to be stored.