Swiching ipod, trouble with library

Okay I started using an Ipod waaaay back in the day and when I was first using the software everything showed up in the itunes library i went from an ipod mini to a nano, and all i had to do was click and drag the music from the library to the nana icon.
So a couple of years ago my old ipod went bust and my parents gave me a new one for Christmas its a 2nd gen ipod nano its started having trouble where it would only turn on some of the time so my mom gave me her old ipod, when she got a new one, the one she gave me is a ipod nano 3rd gen
so here is my problem, when i was using my 2nd gen nano none of the music i have that is not purchased from itunes shows up in the main library (the one that shows even if you dont have an ipod pluged in) a lot of these songs are from CDs but i dont have a lot of those CDs anymore, the whole reason i use an ipod is because im really hard on my CDs and they always end up so scratched they wont play anymore. Anywho so i'm not sure how to get those songs from my 2nd gen nano to my 3 gen nano because in the past when i went to burn the music to a disk it would only want to burn the music from the main library.
any help or suggestions would be great appreciated.

Not sure it is the case but you might want to check if you have unecessary top and left properties that are on the timeline but unused. If so, delete these lines.
See an example of this behavior in this example.
https://app.box.com/s/m3cahj48n8rd7ul8acf1
Preview it. Drag each square and see what happens.

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