iTunes Match and iPad syn

Quite a bit of an issue here...

After googling for a few hours, I am unable to fix my current issue. Hopefully someone with experience can assist with this one.

I have around 4k tracks in my iTunes library in ALAC format and loaded artwork etc. Firstly, when I synchorise with my iPad Air via USB cable (genuine), after the first 1GB or so, iTunes will randomly quit, and thus the process will stop. I have tried this many times and have completely restore Mavericks (Macbook 2009). The tracks are stored locally. Secondly, after turning on and paying for iTunes Match (as iTunes Radio has arrived down under), iTunes would quit. This normally occurs in Step 2 and around 500ish/ 4000ish tracks.

My best guest at the moment is that there is a track in my library that's causing the issue.

Without having to rebuild the entire libary from scratch, ie. saving the tracks onto an external HDD and then adding them slowly, and running iTunes Match after adding 200 or so tracks.... is there a way to figure out which track is the issue?

Any help here will be much appreicated.