Hi Hunter,
Thanks for the reply. I was able to find a solution, so you can pass it on to others that may experience the same problem (even though it sounds like this is an isolated issue). I added some custom wp-admin CSS into my child theme functions.php file:
//CUSTOM WP-Admin CSS
add_action('admin_head', 'my_custom_admin_css');
function my_custom_admin_css() {
echo '<style>
.ui-dialog .ui-dialog-content {
overflow: visible !important;
}
.supports-drag-drop {
z-index: 10000010;
}
</style>';
}