Switched to Linux - now I can actually program the DigiSpark! The final result is a HID keyboard, so shouldn't have the same driver issues.
I have a test working now, with a digispark and tiltswitch producing keystrokes as I move it. Currently it sends 'a' and 'b' so I can see what's going on, but the final version will be something like Shift-Win-F9 and Shift-Win-F10.
The software side flips nicely when a dialog button is pressed - next steps there are:
- Something to draw a diagram of the screen layout so you can pick which monitor to rotate visually.
- Register global keyboard shortcuts for those two keys.
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