Windows can be frustratingly inconsistent about what is too long for a file name or directory name. Different applications, utilities, and built in file functions all seem to have different ideas about what is too long. Even when moving files from one NTFS drive to another NTFS drive.
I've gone with a solution where I have custom "Rename, Move & Copy" files rules in JRiver to trim the names down to shorter lengths that are long enough for me to be able to read and know what the files are yet short enough to be able to copy to different drives without getting errors. My renameing rules have evolved over time and have gotten more complex over time. Here's what my rules are to give you an idea:
Directory rule:
[Library]\[Album Artist (auto)] - [Album]IfElse(!IsEmpty([Disc #],1), -PadNumber([Disc #],2))
Filename rule:
if(isequal([media type], Audio), Mid([Album Artist (auto)],0,20)-Mid([Album],0,20)-If(IsEmpty([Disc #],1),,PadNumber([Disc #],2))-PadNumber([Track #],2)-Mid([Name],0,20), [Name])
[Library] is a custom field equal to "Rock, Jazz, Classical, Country" and a few other general classifications.
I use those rules to rename everything in my library and I've had no more problems with file names being too long.
