When you look into the capacitors from the left side, you can only transform to a higher impedance. When you look from the right side towards the inductor, you can only transform to a lower impedance. So when using the design formulas, the impedance on the left side must always be lower then the impedance on the right side. It doesn't matter on which side the source is (so you can put it on the right side also).
Similar situation you will encounter with the "L matching netwok" containing only one L and one C. When you look into the series component, you can only transform to a higher impedance. So when you need to transform to a lower impedance, the source needs to look into the parallel component (component that goes to ground).
In the past (when using vacuum tubes) you mostly needed to transform a high anode impedance (up to kOhm range) to 50 Ohms. Now with low voltage RF power applications with BJT and MOSFET, you need to transform some Ohms to 50 Ohms.