I just noticed that if the game fails to run in the simulator because it cannot load the dynamic shared library, you cannot use the shortcut to upload the game to the playdate. In this case you need to mount the playdate and copy the pdx yourself.
(technically the "Upload Game to Device" work but when the console try to launch the game the console says run /Games/(null))
It only happens for game using C but that would become a much common issue when games would be shared more often. So a game build on windows will fail to load on a mac simulator, and even a game build on an Apple Silicon machine might not work on an intel one.
It would be nice if the simulator would not just fail but show at least the launcher card with a message that says the game cannot run on the simulator (on the simulated playdate screen, not the console) and that "Upload Game to Device" would still work properly.