Caveat emptor, good people !
I just found over a dozen recordings which were lost in my automated file backup system due to
very complex naming conventions.
This includes some commercial releases, with file names that contained venue, date, Band, set, and identifiers for guest artists.
The Windows NTFS filesystem should allow up to 255 characters, and the Windows versions should support this.
My finding is that the version and patch levels of Windows, Mac OS, and Linux may restrict this greatly.
Different file managers handle the names differently.
In short, for Windows, Total Commander (aka Windows Commander) and SyncBack will span Windows versions better than Windows xcopy, copy, and move.
In summation, Robocopy is a Windows copy command worth learning.
(Didn't expect the surprise ending, did ya?)