iPod Transfering music iPod Nano 16GB

i just got a 16GB nano to replace my old 30GB classic. as a result of having the classic, i have far more music in my itunes than fits on the nano. due to this, i set my new ipod to only sync checked songs. however, after hooking up my ipod and the transfering supposedly being complete without issue none of my playlists transferred (except a 2000 random-song list of "ipod selections" in the playlist section) and some artists (yes, they were checked) were randomly skipped. any suggestions on fixing this? i'm using windows. thanks!