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.

With the ipad, there is a new music app that came with iOS 5.0x.   New GUI, etc.  It also is buggy.  I often have it crash and have to restart while playing music, scrolling etc.
With match, if you have a lot of songs (I had 13,000), it takes a long time when it is first turned on and the screen from what I recall was blank .  Long time being 10-20 minutes if not longer until it is complete.  For the first 10 minutes all I saw was the names of existing songs in the list (and they stayed since I matched them).  Then it updated the list but had not art.  And this was on a wifi N TimeCapsule with 30 down 5 up broadband connection.  You should see the little circle going in the status bar next to the signal strength.  As long as that is going, let it do its thing.  Also, about half way thru you will see artists/albums start to list but no art  Art seems to come last.  It's best to just let it sit and do its thing.   The art eventually does come down.   iPhone 4s also took some time (like 10 minutes) but from what I recall was a little faster than the iPad 1.    Do this plugged into the charger.
Once it is complete, it works fine.  Downloads fast, plays the songs etc.  Some cover art goes missing at times for whatever reason but if your turn match off and on it comes back (and yes, it takes another 10-20 minutes to restart match - just leave it on).    I also get the typical music app crashes but I got those without match too.  Hoepfully it will stabilize with the next release of iOS.

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