When i stumble on tracks that get errors i single them out and put them in a dedicated folder. Start to "wash" the tags and search for things that i know make mp3, flac or any other "container" behave strange. If that wont work. I recode them, first as non lossy format to get rid of the artifacts that make the errors. Please note that this does nothing for the quality, but just rid the algorithm in the compression. I prefer wav. Then i look at the file in an editor. Sometimes long pauses or cuts can make the file unplayable. Just because you have Autocue does not make it foolproof. I recode the file to its original state. And in most cases the file plays like normal.
Also, make sure to always rip or convert into 320 CBR. I don't care what other guys say, that CDJs, XDJs, accepts mp3 in VBR. To me VBR sucks, always have. that can be a culprit as well
If i can't get this to work. Get another copy of the same track, if possible!
Ive noticed one thing that makes this happen. 1. Eject Usb without "Safe ejection" Just pull usb memory out or turn of power. Not so frequently with SD, because of the safe eject with the lid. 2. Also when you export a playlist with and external source. Make sure that the music in fact are exported. Ive come across issues when the "Data" has been corrupted and exported but not the music itself.
Hope this info helps!
/M