Some of my tracks in my iTunes library (eg: audiobooks, lengthy classical music pieces) only play for either 6 or 8 minutes then halt. Why?

So if there is a track that would last longer than 6 or 8 minutes, the track simply stops playing.
My library has been built over 6 or 7 years, contains no illegal music, 85% bought from iTunes, rest is ripped CDs. I have transferred my library at least three times from laptop to laptop as I have upgraded machines, and used different account names and passwords as I have moved around in my job. As an aside, every time I transfer the library it screws up, always the audiobooks and always the classical music and how I have it all catalogued.
I am asuming it's a iTunes library problem, not a problem with my iPod classic?
All help and advice gratefully received; thanks.

Actually I think that its a problem with either the gapless data or the song volume settings that has been brought by itunes 7. When adding new files to the library, iTunes takes a while to determine volume/gapless information. I have replaced files and itunes didn't check the volume and info again, that is why every song stops playing at the last 40 seconds only on the iPod.
I re-added one of the bad files and it played perfectly, but I don't want to lose the data on the other 60 odd files, so is there a way of forcing iTunes to recheck these files? (otherwise i'd have to re-rate and play the songs to the level they are right now)

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