How to I deal with the **** grey dotted circle?

I'm really getting annoyed at this. Everytime I sync it says that a file cannot be read when I try and put the songs on it, so I unchecked automatic sync so I could manually put the songs on my iPhone 4. Everytime I do this and try to get my full library onto my iPhone, it is random different songs that iTunes cannot 'read', sometimes it will be songs that it previously put on my phone, it's getting ridiculous and it is clear that it is not the file but iTunes since otherwise the file would never have been sucessfully read. I even redownloaded an album from a CD, and they all went on my iPhone.. But when I tried to change the artwork of all 15 songs in the album, 1 of them 'couldn't be read' and is no long able to be played.

Is there anyway to fix this, and more importantly is there actually a way to remove the songs with grey dotted circles and greyed out names from my iPhone so I can try redownload them and see if that works? It is getting ridiculous how difficult it is to even delete a song that won't work from my device.