Probably your idea can be complemented using the same idea already used in the QuickPaste assistant (even if its not working as expected. I need to fix that bug). When double clicking the History or File item, old field metadata data will be overwritten, if at same time Ctrl key is down, new data will be appended to old one, if Shift key down, new data will be inserted before old one. If metadata field is in edit mode, only the selected text will be replaced by the new one.
Drag and drop can use another approach. When drag cursor hovers field, all old data will be replaced by dropped one. If user delay the drop by one second, field will enter edit mode and cursor positioned at current mouse pointer position. When dropped, new data will be inserted at cursor position.