I wrote a plugin named »Dynamic Image resize« for exactly that purpose. It features a template tag and a shortcode (that takes the exact same amount of arguments, the template tag takes.
// The args need to be an array
dynamic_image_resize( array(
// The full path to the image in your uploads folder
'src' => 'http://example.com/wp-content/uploads/2012/03/some_image.png'
// OR: the ID
'src' => 6
,'width' => 60
,'height' => 100
,'classes' => 'some classes to align and style the image'
) );
You could even make it even easier and add a “child”-plugin that offers a TinyMCE button.