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Is it difficult or impossible to transfer a book published in
InDesign 2006 to the latest version?
Just open it. Some text might reflow if you edit it but other than that it should be fine.
To avoid surprises, you should go ahead and FORCE the text to recompose after you open any file that old in a new version.
On Mac the shortcut is Cmd-Opt-/ (forward slash), on windows Ctrl-Alt-/
Better to see any oversets or bad breaks at the beginning than to find them in the proof.
If you were using Type 1 fonts in your old files, you will get warnings about them being unsupported soon, which will mean you will have to replace them with OTF versions (if available). This may cause reflow as well.
If you have a PDF of the old 2006 file as it exists now, keep it around; it will be a handy reference in case you need to adjust your text when you convert.
if you have a PDF of all pages of that book you could import all PDF pages to the document you opened in the new version of InDesign. That would you show you the differences in reflow. Put the PDF pages on an extra layer you could "blind out".
For placing the PDFs automatically use the MultiPageImporter script:
Note the option:
[ x ] Place Pages on a New Layer
( ACP )