None of the watch buttons or the buttons in Simulation > Activity Data window trigger any of the callback functions on a DataField. The same code with the same SDK version did work in Linux, so this seems to be a bug in the Mac implementation of the simulator.
SDK 4.1.7, MacOS: 13.1
I found some similar issues but none is exactly the same:
https://forums.garmin.com/developer/connect-iq/i/bug-reports/ciq-simulator-time-simulation-does-not-work-on-mac
https://forums.garmin.com/developer/connect-iq/i/bug-reports/sdk-4-1-1-simulator---activity-data-simulation-do-not-support-button-press
https://forums.garmin.com/developer/connect-iq/i/bug-reports/simulator-in-sdk-4-0-6---removed-support-for-activity-simulation-for-widgets-and-watch-faces