Why won't my ipod 5 sync any music since i updated itunes to 11.3?

About two days before I updated to itunes 11.3, i downloaded some mp3 songs to itunes then to my ipod, and they worked perfectly. then i updated itunes from 11.0 to 11.3, made a playlist out of those latest songs, & tried to send that playlist to my ipod. Only one of eight of those songs work now, even though they still work perfectly on itunes. i get a dotted circle next to the songs on my ipod, and no matter if it's connected with a usb or over wifi, those dotted circles never change.
i've tried deleting anything off of my ipod- songs, photos, apps, etc- but now anytime i delete a song off of my ipod, i get the dotted circle if i try to send it from itunes to my ipod again. I have about 4gigs left of space. I really don't want to restore my ipod, because some of the content on there is not on my computer or cloud anymore.
Any bit of relevant advice would be appreciated! Thanks!

what does the dotted circle mean?
Re: What does the gray dotted circle in iTunes mean?
Dotted circles next to songs, won't sync, red circle with square?

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