How would you do this?

Hi!

Im working on a theme for one of my clients.

I like my clients to be able to

1) manage the content in an easy way (without knowledge of HTML/css).
2) Add new pages thats based on a template of mine.

I want the template to look like this: http://bayimg.com/MABNBAADP

There should be different images to the right for each page, how would you do to add these in a smooth way? Since i dont want to have divs in the page-editor, it is not an option to have thoose images the normal way in the page-editor.

I’ve been thinking about looping all attachments to the page to the right, but that would hinder my clients from adding pictures to the middle column without having them in the right column aswell.

How would you do?

thanks in advance :-)!