Thanks for noticing the update and reporting on it!

The initial status check isn’t very descriptive regarding critical errors, but these error messages can be improved in future iterations so users know how to get to a page with more information.

This depends on exactly what's wrong. Some errors will be more descriptive, as seen here:

https://cloudup.com/cLsCh588VOV

But, we're definitely going to iterate with inline action links, detecting more issues within the plugin (vs relying on the jetpack.com debug and internal tools) for critical issues and offering recommendations, when appropriate.