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In case 2, the line is matched to the transmitter output impedance, and the length of the line doesn't matter. No impedance transformation here. The transmitter will "see" the resistor in parallel to the antenna impedance.

In case 1, the antenna impedance will be transformed to some value that depends on line length and wave length, so it varies with frequency. This frequency dependent (transformed) value will be in paralell to the resistor.

So in case 1, line length matters.

In case 2 it doesn't matter.