[eschwartz]

I don't know about that, but you may want to make use of the series column. If you need the series to appear on devices (none of which, of course, can handle series info) you can use plugboards to set the title whenever you send to device. An example plugboard that would turn:

calibre metadata title ===== Betrayer of Worlds
calibre metadata series === Known Space Series
calibre metadata series # = 4

into: book title on device = [Known Space Series 4] Betrayer of Worlds

would be

{series:|[| }{series_index:||] }{title}

Plugboards: a very useful (yet oddly obscure) thing.
You can read more about them here: http://manual.calibre-ebook.com/temp...and-plugboards

Or at the MobileRead Wiki: Kindle_and_Calibre_Plugboards

This may save you some shortening. It is also worth noting that nothing was broken; calibre simply wasn't able to create a longer filename due to Windows filesystem limitations. calibre still knows exactly where your books are.