Bluetooth Headset Association for Audio Output

I have a business case to supply Bluetooth (Bose) headsets instead of porting the audio out through the monitor speakers. The use case is a loud noisy cafeteria environment where we want to have 5 minute training videos that help provide the focus on the content and not the external environment. Would this be a checkbox in the setup function to push a config down to the Pi 3 B+ device and have auto connect or discovery enabled on the headset?

Unfortunately Bluetooth is not supported at all right now. It would also require a bigger change as the internal signage player software only supports analog/HDMI, not arbitrary output to, for example, Bluetooth or a HiFiBerry.

I think a viable alternative might be to use analog output and combine that with a device that transmits using Bluetooth. Maybe this might work?

Maybe this is a hardware solution, not software. Ref:

Use 3.5 to 3.5 output of Pi 3b+ for two headsets. SOLVED HomeSpot Bluetooth

Worked like a champ, used HomeSpot Bluetooth with MPOW Noise Reduction H10 Headset ($65).

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Neat. Thanks for the update!