I't not just Windows 7.
I have a current gen Macbook Pro running Mountain Lion. Since the update to 11, the sync always stalls at 'Copying 2 of...', so the first track appears to sync before it stalls. I have tried deleting the album of the offending track, and this makes no difference - it doesn't matter what the second track to copy is, it always stalls at 'Copying 2...', and always when the load bar is over 95% along (and it takes MUCH longer to get there).
I have tried unchecking 'convert higher bit rate songs to 128kbps' and instead selected 'Manually manage music and videos' and managed to Autofill my iPod. However, my iTunes library is 210Gb+, so this isn't a long-term solution.