Better Image Insert Workflow

A truly slick configuration of Insert and Image Resize Filter would disable insert if the img tag is not available for the selected text format.

Furthermore, when clicking Insert, it would checkmark the box to not list the file... which doesn't exist for imagefield files. Aw, Drupal, what the hell? Anyway, when an image is inserted, it should not be shown. Usually i did this by not displaying insert-enabled fields at all (under Manage display for each view mode); i guess that can be the approach and people have to learn that they need to insert it, but an either inserted or displayed option would be very sweet.