And dynamic placeholders in what program? On what system? You need to be a lot more specific...
Sorry - yes I do - InDesign CS6 - Windows
Moved to InDesign forum.
You might get at least part of the way there using Data Merge. I'd anchor the image frame in the first paragraph, I think, and apply an object style to fit frame to content. I'm not sure the fitting will actually work -- CS6 is a little buggy on that -- but worth a shot. You'll probably wind up with overset text all over the place, but the Text Stitch script at Rorohiko.com will, I think work to thread all of the merged frames into a seingle story and move the overset to the very end where you can deal with it easily.