It would be nice if the DelayUndoManager provided some standard undo and redo Actions (in much the same way that Cut/Copy/Paste are provided in the DefaultEditorKit). I would expect these actions to update the NAME, LONG_DESCRIPTION, SHORT_DESCRIPTION, and the enabled status of the Action. This way the menu/toolbars always appear updated correctly.
I tried to implement this myself, but found that if I check canUndo or getUndoPresentationName before the DelayUndoManager's timer goes off, the DelayUndoManager will prematurely commit the edits (which defeats the purpose of using the DelayUndoManager in the first place). My only other option is to re-write your DelayUndoManager myself to coordinate the actions better. I don't like re-writing things other people already wrote
I believe if you provided these actions (and a way to easily customize the other attributes of the action like menumonic, accelerator, and icon), your DelayUndoManager would be much easier to use and provide menus/toolbars that work great.