Currently for drawing model annotation groups, if the user wants to update the annotation, they would need to remove the outdated annotation group, which would removal all annotation groups, and then reapply all annotation groups. It would be nice if the user could say, update all applied annotation groups.
If you're loading annotation groups from a dgnlib, you can rightlick on the file in explorer and "update standards from dgnlib". I will say this isn't perfecct but it works most of the time.
I'm confused here a bit... Annotation is/can be automatically updated by ANY design changes... What isn't updating for you? If anything, more work needs to be done on not messing with annotation if nothing has changed combined with improved annotation capabilities that would lessen the burden of manual annotation changes that get wiped out when something is reannotated...