I think USB (MTP) support has more problems on Linux, but that is NOT Calibres fault or a real issue if you pay attention to ONLY ONE at a time.
IIRC there is even a Calibre PI that ONLY supports Linux (and there is no Only Windows PI)
FWIW You can make W10 NTFS folders case sensitive (Google comes up with a number of tutorials), which should help with OS flipping users.
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