Possible to “Attach” images to multiple posts without inserting or uploading twice?

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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