The opto output is a transistor so you should be able to see a lower resistance across the collector and emitter connections (positive to collector) with an ohmmeter when the LED input is conducting.
But it's never a "short".
The maximum collector-emitter current will typically be some large fraction of the LED current.
Your new schematic does not show the polarity of the 20V.
If pin 1 is +20V and pin 2 is 0V then the transistor should turn on and Vout should be low. If pin 1 is -20V then the LED in the optocoupler might be destroyed.