Ok I did some searching & none of the stuff I found helped.

I have a 16gb ipod nano (not even a year old) & the lil bugger is being a pain. See I made this live compilation in FLAC & exported it to MP3 with MAX. When it plays on itunes it plays FLAWLESSLY. All the tracks segue how they are supposed to. But on the nano? Some of the songs don't. This is a pain in the *** considering how much effort I put into making this thing. yes I have "gapless album" checked (though it unchecks itself) & I'm not sure where the problem is...