Need recommendations

I’m looking for a plugin that will allow me to pick an image on a per post basis.

What i envision is a central repository for adding and managing the images then a checkbox interface on each post for choosing which ad to display. This image would be inserted where custom code was added to the template or within the post body.

Ideally i could also have multiple containers per post. For example: Show in sidebar (code added to template), show below post (code added to template), show in post (code added to post body).

Does anyone know of anything that can get me any/all of that?