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75 characters is the limit for the path to the calibre *library* folder not the path to the calibre portable folder, which must be shorter since it *contains* the library folder. And yes, if you used a longer path you may never have run into issues until you finally had a book with a long enough title/author. At which point things would break. To prevent that breakage is why calibre-portable.exe now checks path length limitations.
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