I don't remember if a tilde is a reserved character
The bigger part of issue is Calibre runs on 3 OS, each with their unique issues to avoid What was valid on one may not be on another.
Starting a name with a special character may have a different effect than use in the middle.
I really endorse using old style DOS, allowed filename characters. You never know when you will trip up a bug in one of the many building blocks used by Calibre with those on the edge
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