I have ipod classic, 160gb, with new computer with Windows 8 and latest version of Itunes - came from xp and previous version of itunes - and never had a syncing problem.
All my songs are in new itunes on new computer, however ipod will not sync. Have received -50, and duplicate file name - I restored and it will go so far and then freeze. Or I get -53. Have tried lots of suggestions discovered on pages like these... but none have worked. I do see there is a problem with classic and new itunes - does anyone have any solutions??