It should work but I don't have any headset so can't check.
I've just tested sWM on HTC Kaiser. I've connected and disconnected the watch many times without single problem or error. Only requirement is restart after pairing/com seting. Communication over incoming port is stable.
I've already implemented bitmap -> hex converter so now Im looking for the right fonts. We need:
1) Probably bold and good readable font, height 16 pixels
2) Smallest and readable font, 8 pixels height (for two lined text output)
Dr. Brainiac: Install Resco Explorer with included Registry Editor Plugin. The trial version should be enough.