Why can't I download new music to my iPhone 5s?

I downloaded the most recent software for the 5s and now I'm having trouble putting new music onto my device. I use a youtube to mp3 converter and the music goes directly on my iTunes. It is allowing me to play the music through iTunes, but every time I try to put it on my iPhone it says it is updated but skips right over the song when I click on it and sometimes disappears.

How do I fix this? I just want to listen to some new music!

I have a new iPhone 5 that I want to fill with some music from my itunes library.

1. Under summary I have checked the option to manage my music manually
2. Under music I have deselected 'synchronize music'
3. I have applied these settings

Now, when I drag songs from my itunes library to my iPhone I see a green + symbol when I hover over the name of my iphone.
However nothing is copied onto my iphone, all the songs are greyed out on my iphone. When I disconnect the music app on my iphone says there are no songs.

You can get it directly form itunes or google play.

I have tried adding it directly from iTunes and it doesn't upload to my phone. I've had an iPhone for years, I know how to upload the music it just isn't working and i'm not sure why. Any suggestions?

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