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Originally Posted by Jessehk
This makes sense. I think I'll go with option number 2 (though I already know Python and option number 5 is not completely unreasonable  ).
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Could I change your mind? New eyes and fingers are always welcome!
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Would I have to change all the authors manually or could I automate it somehow (I have roughly 250 different authors)?
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Yes, it is manual. That said, it isn't too hard to do.
The trick is that the author_sort is probably already what you want the author to be. If you open the 'manage authors' dialog (right-click on an author in the tags browser), you can copy/paste the author sort value to the author one by one. This will rename the author wherever that author appears. I did this once for around 200 authors, and it took around 10 minutes. *Be sure* to change the tweak first, or you will be fighting against yourself.
Edit: You might want to test #2 on a small number of books to be sure that the assumptions about both calibre and kindle behavior are right.