I was receiving many of the same errors in my logs, and after about 15+
fixes I tried, this was what ended up working.  My main issue wasn't
really connecting the headset, it was keeping it connected for more than
a couple seconds and being able to play a2dp. Hopefully this works for
some of you.

Go into bluetoothctl and set your device to trust

# bluetoothctl
# devices
    Device XX:XX:XX:XX:XX:XX 
# trust XX:XX:XX:XX:XX:XX

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https://bugs.launchpad.net/bugs/1490349

Title:
  15:10 and 16.04: bluetoothd reports "Not enough handles to register
  service" at start

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