iTunes import doesn't sync playlists properly (especially with smart playlists)

The iTunes play list sync doesn't seem to be working properly for me. Not all my play lists are being sync with iTunes (I have 18 smart play lists in SB and only 17 sync to iTunes). Also, the smart play lists are only sync as normal play lists in iTunes (which I don't really mind) except for the fact that each time I open iTunes, the play lists multiply (the same songs are in the play list many times, e.g. I have a smart play list with 200 songs and after I open iTunes multiple times, it suddenly grows to 1000 songs).

I open iTunes to sync my iPod frequently because I have been using SB to organize my messy library recently.