There is no easy answer to this. You will need to create some overrides for the article/category/blog views components/com_content/views.. on the frontend. You will also need to modify the core files administrator/com_content/models... http://docs.joomla.org/How_to_override_the_output_from_the_Joomla!_core
Your best option really is to put the image in your article using the editor and adding a link to it with the editor. You would be looking to do a very time intensive task. You can the assign a css class to the image and float or size it however you wanted.