How do I get all my music to sync to my phone?

I am trying to sync a playlist of 104 songs to my iPhone, so I select the playlist under Music and Sync. However, on my iPhone, only 32 songs are synced. I tried restarting my iPhone (holding home and lock button), reinstalling iTunes, and unsycning all my music then syncing the playlist again. I have a MacBook Pro Mid-April 2010 edition with the latest version of iTunes and iOS software.
I also have a problem with my iPod (just including in case the problem is related). All of my music is shown, but when I play a song, depending on which song it is, it'll either not play the song or skip to a different song. I have an iPod 4th Gen black.

For your purchases, read this:  iTunes Store: Transferring purchases from your iPhone, iPad, or iPod to a computer, http://support.apple.com/kb/HT1848
For other content, you need to transfer from your old computer to the new Mac or use a third party utility like http://www.ecamm.com/mac/phoneview/ that can get it from your iPhone.

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