As you’ve noted it’s not possible out of the box. The feature was supposed to make it into 2.9, got postponed until 3.2, and assuming they reject the post2post table mike and I crave for it’ll probably be postponed again.
You’ll have better luck creating a custom taxonomy in the meanwhile, and “tagging” images tied to this or that post accordingly. That’ll give you an n-n relationship.
As for difficulty, I’d say not easy. Adding extra fields in the media upload/insert screens, in so far as I’ve experienced it (i.e. a huge media plugin) is a bloody mess.
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