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It could be required that Calibre performs moves of its own library, and therefore manage filename length calculations and renaming as necessary. That seems like a proper concern for Calibre, rather than assuming users be allowed to move its files by other, external means.
Often a book title has critical words near the middle or end of its title, and it's those words that can be truncated by Calibre's file renaming.
The variety of file system limitations on different platforms is I agree a problem. Those limitations could be built into Calibre perhaps; perhaps also there is a file system abstraction in the Python or other libraries used to build Calibre? I also think this effort is worth some consideration based on the sheer number of Calibre users who have complained about this issue over the years.
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