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I'm only a beginner with Writer2ePub. Haven't discovered all tricks and functions yet.
The more complicated a document is the more things seem to go wrong, at least for me.
As work around, you could put a place-holder where you want a picture (something that is not used in the text, like *, +, ~) then open the epub with Sigil and put in the pictures there. I found that much easier than trying to find out what went wrong in Writer2ePub.
When you have many pictures, best enumerate the place-holder *1, *2, *3 and the picture 1.jpg, 2.jpg, 3.jpg. With the search tool of Sigil you can jump right to the next *.
I hope this helps, or someone comes around, who can explain, how to solve the problem with Writer2ePub.
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