I believe the limitation is cross browser compatibility. The pop-up window that opens up to ask for more information is a function of the browser and many browsers do not support more then one option in that space (simply how they were designed). If the page that opened up happened to be HTML then it would be a different story (but it's not). At this point the software
is pretty much stock when it comes to the WYSIWYG post editor and although your idea would be nice, it's not as easy as just being able to add it and making it work across a handful of browser and various version of those browsers as well. If the software
ever changes the way it handles this, I will certainly explore how we can do this without causing upgrade issues. Thanks again for the feedback.