Incomplete Playlists

I can’t get the complete playlist to load.  It’s 422 tracks long but when loading it hangs up around 200 to 275 tracks into the sync and just sits there.  When I disconect the player it has thoses 200 to 275 tracks and they are in order.  Any ideas.  I listen to audio books.  I rip them from CD’s from the library to wma files using Nero.  Then I build a playlist on my PC using RealPlayer.  Then I highlight the playlist title and hit transfer to device again using RealPlayer.  I’ve had luck with complete playlist transfers when they are less than 200 tracks but never with the larger playlists.