That's the best I've come up with so far. If you require a password to wake the system and have it set to immediate, changing it to 5 seconds allows you to immediately sleep/wake the system without having the reenter your password. I literally wait for the screen of my Thunderbolt display to turn off and immediately wake it back up. Connecting my headset and briefly putting the system to sleep via the Apple menu.Dedicated headset that stays connected to the system (not really an option for you).I've been struggling with the same issue as you and I've come up with two solutions.
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