I’m not sure how difficult this would be to implement.
Lately there have been a few issues with people’s instances failing rebuild or not working because of broken plugins.
The status of plugins is monitored here on meta.
A third column in /admin/upgrade#/ which indicated “Broken” or “Suspect” would give a headsup to people before they get themselves in trouble.
Even just a “Check status” which pointed to Discourse Meta plugin might be worth considering.