Itunes says i dont have enough memory, even though i do

I deleted tonns of music off my iTunes, and when I decided to sync my iPhone, it told me I didn't have enough memory - even though I was syncing less stuff than what was already on the device. I originally had about 1000 photos synced to my iphone from my laptop, which I removed. I have around 2000 pictures on my iphone, but it's telling me Im syncing 3000. I've deleted about all the photos I can bare to and it's still telling me I need an extra 4GB. When I'm sinking and I look at the bar telling me what is taking up memory, it says I have 14GB free - but yet I'm still getting an error saying it can't sync because I need 4GB of memory freed up. Can anyone help me?

What happened prior to this?  I suspect some important details are being left out.

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