In Insert Object dialog, add a checkbox Use Current Selection as Default without Opening Dialog (Shift+click to open dialog).

Select this option will not open dialog from next time. But user could still hold shift key to open dialog to change selection or uncheck checkbox. Once this checkbox is selected, 2nd line of button tooltip could be Hold Shift key to open dialog.

This checkbox will be available for “Create New“ choice only, and it will not be saved for the “Display as Icon“ choice.