Douglas
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I had a book for PDF distribution I originally created in 2009 and didn't touch it until I decided to create a print edition. I updated every file, had to relink things, etc. Everything worked. Preflighted green. It's a 370pp book with about 200 linked files. Each page has at least 3 linked indesign files.
Preflighting worked. I went to print to pdf from the book menu and it would get to say p40 or so and then ID would just disappear crash. I watched what page it was on and started to break down the print to where ID crashed. I could isolate docs that caused the crash, but then I could always print just that doc by itself. Then I would grab another small group, try and print, find where it crashed, isolate it, and print it by itself. Made no sense. I spent 3-4 hours attempting to get through the book feeling something else was wrong. I have a huge series of books to produce in a similar format, so I didn't want to do this goofy one by one solution.
I read on another forum to maybe recreate the book itself. File > New > Book. I did that - got all the single ID files in there. 50+ main files, 370pp. I exported to PDF and all 370 pages rendered to one PDF on the VERY FIRST TRY.
I recommend creating a new book! Though I had saved it many times, letting ID update it over the years / versions, there was some cruft in there somewhere across those versions that simply creating a new book eliminated. YMMV!
The book is the "Big Book of Font Combinations" if you are curious as to why I needed so many ID files. They are layered on each other, and mixed-and-matched. Print version on Amazon / BN coming shortly!