I've tried every Playdate SDK since the original release and the simulator still doesn't work for me. The window just opens with a frame and blank contents, and then closes a few seconds later. No error messages or anything.
Event Viewer just shows the following
Faulting application name: PlaydateSimulator.exe, version: 0.0.0.0, time stamp: 0x62351ba5 Faulting module name: PlaydateSimulator.exe, version: 0.0.0.0, time stamp: 0x62351ba5 Exception code: 0xc000041d Fault offset: 0x000000000000d2a2 Faulting process ID: 0x8a4 Faulting application start time: 0x01d8486aee1a87a7 Faulting application path: C:\Users\[me]\Documents\PlaydateSDK\bin\PlaydateSimulator.exe Faulting module path: C:\Users\[me]\Documents\PlaydateSDK\bin\PlaydateSimulator.exe Report ID: a2c9e033-9f63-4901-9e3a-c62d978a016b Faulting package full name: Faulting package-relative application ID:
So that's exception code
0xc000041d which is apparently "An unhandled exception was encountered during a user callback." according to what I can find on Google.
Seems like a bug in the simulator. Hopefully there's enough info here for you to fix it.