A good post, thanks. Here are a few notes and questions for clarification.
The reason it went into compass calibration mode after you reduced the time to start to 3 minutes is that it detected that you were within 4:30 of the start without having set the wind. It does another check at 2:30 and then, if still no wind set, at 2:30 after the start. Having an initial wind is that important for it to know your point of sailing. Once it has an initial wind, it does a pretty good job of re-calculating the wind as you work upwind.
Why it hung in the wind screen is a worry. You don’t say whether you attempted to set the wind at that time ( pressing the SELECT button) so I am not clear about the nature of the hang. You say you successfully backed out – just with short BACK presses?
And the hang when you went into the real start is also a bit of a mystery.
Can I ask you to try those steps again (off the water, but with the phone receiving a GPS signal) to see if you can replicate the problem please?
Glad you’re enjoying the dashboard and I’m sure the folks at pebble will be delighted that we’re boosting their sales!
As a fellow software developer, you will be familiar with the challenges of getting code to work in all environments, so you will understand the need for comprehensive error reporting.
BTW which watch and phone are you using?