When the date-data field is used in conjunction with the "now" parameter, the date updates the first time edit contents is used but then does not update after that. Is this expected behavior? Has it always functioned this way?
The parameter "now" in date-data macro is actually the default value you can use for date-data macro. After you edit content and save the page for the first time, the date-data will pick the time that you first edited the content.
After that the value will be stored in scaffolding xml and the value after that will not be updated according to your real-time as it will pick up the data from scaffolding xml instead.