When I add songs to my ipod 5th generation the songs don't add, why is that?

I keep adding new songs to my ipod. It seems to work but then I leave my house and the song isn't on my ipod. I've only had this ipod for about 3 weeks. Prior to this ipod, I owned another ipod 5th generation for about a year, but I lost it & I never encountered this problem with that ipod.
the song shows up greyed out when i click my ipod from my itunes like this:
& isn't on my ipod once i disconnect it. It seems to be adding the songs slower or something. Also, sometimes when I attempt to add one single song to my itunes my whole library gets added to my ipod, which is annoying because I delete songs from my ipod, yet they're being added again.
Is this apart of the update? Is there some way to fix this to the old settings because I tend to get music from other people's itunes libraries too, and i don't want their library syncing on my ipod.

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