Listen to the "pre-listen" output on the monitoring output.

Is it possible to hear the PFL output on the monitor output?
Currently, I can hear the main output via "Line 2" (provided "monitor mute" isn't active), but I would also like to hear the PFL (soundcard output 11-12)—specifically the pre-listen player, the track tool, and the segue editor. My plan is to use output "13-14" for the main mix, output "11-12" for the secondary output, and "Line 2" for monitoring.

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It shouldn't, the same device can be used in different places. Ensure that you don't select the "Exclusive" mode.
I understand that the same device can be used for different outputs, but if I set both "monitor soundcard" and "preview device (PFL)" to the "[WASAPI] Line 2" output, I lose the audio from "[WASAPI] 11-12" because it won't be assigned to any output.

I need to hear "Preview device (PFL)" on "[WASAPI] Line 2" and "[WASAPI] 11-12" simultaneously.
 
I need to hear "Preview device (PFL)" on "[WASAPI] Line 2" and "[WASAPI] 11-12" simultaneously.
I'm sorry but this is not supported, RadioBOSS can only use one device for PFL. You can use different methods to copy audio from PFL (set in RadioBOSS) to some other device, I believe Audio Repeater should be capable of it: https://vac.muzychenko.net/en/repeater.htm
Some audio cards have audio routing configuration in their control panel/virtual mixer, as your card has output names like "11-12" it's likely that it has this feature.
 
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