I wrote a pretty long Tag > Filename script that truncates the Title so that it fits within the 256 path and filename character limit of Windows.
Here it is for anybody that is interested:
$num(%track%,3) - $validate($replace(%album%,.,-),-) - $iflonger(%_folderpath%$num(%track%,3) - $validate($replace(%album%,.,-),-) - $validate($replace(%title%,.,-),-).%_extension%,256,$left($validate($replace(%title%,.,-),-),$sub(230,$len(%_folderpath%$num(%track%,3) - $validate($replace(%album%,.,-),-) - ))),$validate($replace(%title%,.,-),-))
Basically it'll look like this:
001 - ValidAlbumName - ValidAndTruncatedTitle.flac
This script also cleanses album names and titles of periods and replaces them with dashes. I've had failures on some classical albums where the title is more than one sentence and has periods separated by spaces.
I arbitrarily chose 230 as my high-end character limit, which gives me some wiggle room if I have to rename or add a directory or two above the files.
I think this would fail if the path and album name already exceeded 256 characters, but in my case that would be an insanely long album name.
Hope that helps someone.
Adam