I opened a feedback assistant bug report. The id is FB8698815.

I already tested the new "Items" property. Sadly it doesn't work with "HasUpdateAvailable" either.

FYI: It's fixed in iOS 14.2 Beta 4

Thanks for your reply. With iOS 16.1 the device is now correctly updating its' "passcode.is-compliant" and "passcode.is-present" states but it seems that it still won't reevaluate the corresponding activations. (I waited for ~5 hours for the device to reevaluate the activation) If the device doesn't reevaluate the "passcode.is-compliant" / "passcode.is-present" activations until tomorrow then I will submit a bug report.