In regards to the "Plugin Errors" always being displayed in the Settings window now even when there are no errors, possibly you could give visual cues when there is something to look at and when there isn't? When I see a warning triangle there I instinctively want to check it out every time I open Settings even when there is nothing wrong.
Potentially you could show the plugin icon without the warning triangle when things are fine or with a green check mark, display the warning triangle when there is interesting output to look at?