You can develop first with the simulator, then transfer it to the watch.
http://www.getinpulse.com/simulator/Also, you shouldn't have to repair to send an update.
Things to try (in this order):
- kill L2CAPServer and start it again
- reset watch by holding button for about 6 seconds
- reset to backup firmware by holding for about 20 seconds
Try loading the firmware after each of these steps.