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What are some ways of configuring an OSX box to use wideband bluetooth audio from a bluetooth headset for mono input at the same time as using the headset for mono output of system audio, and how would I do this with more than one paired bluetooth headset at a time?

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You might use Soundflower to convert the input to mono. See this question. You might also need to create an aggregate device in Audio MIDI Setup.

The Accessibility (or Universal Access) preference pane has an option to convert audio output to mono.

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